Voyeur to Couple Ch. 02

Between the drinks and already cumming twice, it wasn't long before I was nicely asleep. Saturday passed without any real excitement and then just after supper Sunday, I heard my phone beep with a text. I was kind of hoping it was Deb but when I looked, I was even more excited. "Hi, I'm a friend of Debs and she gave me your number, apparently you met her at the Karaoke. I was the red head that was there with her. She told me you were really good with your tongue and open to things that most guys aren't. I'd love to chat... Claire."

Wow, I'd been thinking that I might be able to find a way to meet Claire through Deb but hadn't expected an invitation that easily so I quickly typed back, "I definitely remember you! Sexy redhead, slim with a great smile. I don't have anything on this aft so we could chat on here or maybe even in person if you'd like."

If really hadn't noticed her smile that much but I'd never met a woman who didn't like to be complimented on her smile. Less than a minute later I got a reply of, "Good memory! I'm not doing anything either, we can definitely get together somewhere close. Maybe send me a face shot so I'll know who I'm looking for."

I took a quick selfie and sent it to her along with where I lived. "Wow, you're really close to me, I'm at the dorm just north of you! There's a bunch of picnic tables between us, I need to grab a shower so how about we meet there in about 30 minutes?"

After sending back a quick, "Perfect, that gives me time for a shower too. Looking forward to seeing you!"

Just in case we came back to my room, I hurriedly cleaned it up, put the telescope in the closet and made sure there was no indication that I'd been watching anyone from my room before heading out. I only had to wait a few minutes before I saw her heading my way, I'd seen her naked from a distance but even though she was clothed, she looked just as sexy in person and even though it looked like she was wearing a bra, her nipples still showed clearly through her t-shirt. I figured from her first text that she wasn't looking for a study partner so when she got to me, after a quick "Hi", I gave her a hug but decided that it might not be a good idea to give her a kiss just yet. She took care of that by hugging me back and giving me a short but full kiss before we sat down.

We were both slightly nervous so I figured I'd get things rolling by saying, "So, you said that Deb enjoyed my tongue but what were you talking about that I was 'open to' that most guys weren't?"

She hesitated a bit then said, "Well, I think she told me everything that the two of you did and unless she was lying, you made her cum a whole lot more with your tongue than most guys do with their cock."

I had to grin at that and said, "She definitely came a lot and I thoroughly enjoyed doing it. It might be a bit forward but I'd love to show you if you'd like."

Claire seemed to blush a little before saying, "Well, that's part of why I texted you, it's been a while since I've been with a guy who would even go down on me, so even one orgasm from a tongue would be an improvement but that's not what really got me interested."

I had an idea where she was going to go but left it to her with, "So what was it?"

"Well, she told me that while you were fucking her, fingered her ass and then when she sucked your cock, she fingered yours. Neither of us have ever had a guy open to that before and that got me a turned on. I'm not sure of any other way to put it so I guess I'll just say that I love to feel a finger in my ass and I've always wanted to try the same thing with a guy's ass but haven't had any takers. I guess what I'm wondering is if you'd like to have a bit of ass fingering fun together?"

"That sounds like a great idea and I'd love to give you a nice long licking as well."

"Mmmm, I was hoping you would. My roommate, Laurie is there though so we'll either have to be really quiet or go to your place."

"I'm pretty sure Sam is gone until after supper tonight so my room sounds like the best bet."

As soon as my door shut behind us, we moved together for a longer hug followed by an even longer kiss. Once we were in my bedroom, it wasn't long before her t-shirt and shorts were off as were mine but unlike with Deb, neither of us were in a huge rush, so we enjoyed touching and kissing as the rest of our clothes came off. When her bra dropped, I realized just how long her nipples were and when she saw me looking, she said, "I know, they're freakishly long aren't they?"

"Yup, but sexy as hell!" and to prove it, I spent the next few minutes playing with one while I licked and sucked on the other. The more I sucked, the harder and longer they got and by the time I finally pulled back, they must have been 3/4" long and very hard. Of course, by now, I was very hard too and after feeling my cock through my boxers, Claire eased them down and off so I was able to step out of them. As she stroked my cock, I went back to kissing her nipples but also eased her panties down with my other hand. I'd seen her pussy so many times but actually running my finger the length of her slit and feeling how damp she already was made things a whole lot better.

Once we were both naked, I guided her back so she ended up sitting on the bed and I proceeded to kiss my way down from her mouth, to her wonderfully long nipples, along her belly until I was face to pussy with her and totally enjoying the taste of her pussy as well as the soft moans and other reactions I was getting. Her first orgasm didn't take long and other than a bit louder a moan followed by a soft, "Oh, I needed that!", it would have been hard to tell that she'd cum. Apparently getting the first one out of the way, was all it took to open the door to a couple more over the next 10 or so minutes and both of them were much louder than the first and they started with a quivering, then she'd arch up as much as she could against my face and finally I could feel her pussy contracting against my fingers or tongue.

Even though I already knew, she'd told me she enjoyed a finger in her ass so after the third orgasm had passed, I let a fair bit of saliva run down her pussy and started working it around and into her pucker. When she felt my finger against her pucker, after laying back on the bed to give me better access, she moaned even louder and I heard a soft, "Yes, right there!"

I was quite happy to keep going and by the time she came again, I was sliding one slick finger in and out of her ass while I kept licking her pussy. Knowing that she often used a toy that was much bigger than one finger, I gently slid a second finger into her ass, two into her pussy and then focused my licking and sucking on her clit. I'd watched her have some pretty intense orgasms through the telescope but when she came again it rivalled the biggest one that I'd seen. It was a good thing we hadn't gone to her place because her moan was loud enough that her roommate would definitely have heard her and I was pretty sure it could have been heard in the hallway. Her body did more than quiver, it almost shook and when her orgasm peaked, she blurted out a loud, "Oh FUCK!" and for the next 30 seconds or so, I could feel a series of rapid contractions from both her ass and pussy on my fingers.

When she finally calmed down, I moved up beside her and she pretty much attacked me with a string of passionate kisses before laying back on the bed with a big smile on her face. "Oh God, if that's what you did with Deb, no wonder she said you were so good with your tongue."

"Well, she definitely didn't cum as hard or long as you did but that was with one finger in her bum and my tongue on her pussy."

"Well, I'm glad you gave me the 'extra' treatment because that last orgasm was amazing."

That's when she stopped for a few seconds before continuing with, "Deb said that you enjoyed it when she slid a finger into your ass and that you'd fingered your own ass before so I was wondering...." and she kind of trailed off.

I figured she wasn't sure how to ask so I said, "were you wondering if you could finger my ass?"

With a slight shake of her head, she hesitantly said, "No, I was wondering... well hoping actually... that I could watch you finger your own ass. I've watched a bunch of videos of guys doing it but would love to actually see it in person."

She was looking at me as if she was fully expecting a 'no' so I think she was a bit surprised when I answered, "Sure, but there's one condition."

"What's that?"

"That I get to watch you finger your ass at the same time."

With only a slight hesitation, she said, "Deal!" and reached for the lube beside the bed.

I know I was nervous and I think she was too but it wasn't long before we were half sitting up, facing each other. I was sliding a slick finger in and out of my ass while I watched her do the same with hers. As we relaxed more and started to get into it, I noticed that Claire had added a second finger to her ass and when I looked up, she was squeezing and gently pulling on one nipple and then the other. When she noticed me looking, she raised her eyebrows and cocked her head to one side as if to say, "Well?"

I took her hint and with a bit of lube, I added a second finger to my ass as well. By now we were both breathing a bit heavier and moaning slightly so I decided to take it one step further and while she watched, I added a third finger to my ass. I didn't often use three and it took a bit to get all three inside but anytime I did, it felt amazing. I was watching her face the whole time and I could see her eyes open a bit wider and then with a quick lick of her lips, she slowly added a third finger as well. I was hard as a rock, with precum running down my shaft and while she wasn't fingering her pussy, she'd occasionally move her hand down to open the lips and show me just how wet she was and eventually she started fingering her pussy and rubbing her clit. As I watched her, I was getting closer and closer to cumming and started stroking myself even faster. When she saw me speed up, she grinned and sped up herself. Our timing was almost perfect because we both came at almost the same time. I left a pool of cum on my belly that was running back down and her pussy was definitely wetter than it had been a minute or two ago. After we relaxed for a few minutes, Claire looked at me and said, "How long before you're able to go again?"

With a grin I replied, "Well, depends on how much help I get!"

She grinned right back and shifted so she could stroke my softened cock a few times before taking it into her mouth. I'd had girlfriends give me head after I came but only if I'd washed or at least wiped the cum off. She didn't seem to mind and from the way she was licking and sucking on both my cock and the cum on my belly, it seemed like she quite liked it. It took less than 5 minutes before her 'help' had me fully hard again. It wasn't long before she was straddling my re-hardened cock. Now that I'd cum, I knew I'd be good for a while so as she rode me, I enjoyed playing with her lengthy nipples as well as sucking on them whenever she leaned close enough. Her pussy was wet, snug and if I looked down, I could see her lips clinging to my shaft whenever she rose back up again. Neither of us were in a hurry and were just enjoying every sensation of penetration, kissing and touching. As she rose and fell on my cock, she slid one hand between us so she could rub her clit at the same time. A minute or so of that triggered her first orgasm with my cock inside her and over the next half hour, she had several more. She must have sensed that I was getting close to cumming because she leaned forward and after a nice long kiss, she whispered, "I'm on the pill so go ahead and cum whenever you want, I want to feel you shoot inside me."

Hearing that was all it took and while I'm sure it wasn't as big as my first load, it certainly felt like it and when she rolled off of me, a trail of cum oozed out and dribbled across my thigh. Noticing it, she wiped it off and then licked her fingers clean which surprised me but in a very good way.

As much as I think both of us would have liked to spend the rest of the evening together, Claire said that she'd head back before Sam got home. After a few more kisses I said, "Understandable, you'll likely meet Sam eventually, assuming that you'd like to get together again."

"Oh, I definitely want to get together again, I'd love a repeat of today and maybe even more."

The rest of the week was spent with classes and assignments but Claire and I texted back and forth each night, having some really sexy talk about how she was looking forward to fingering my ass next time and that quickly progressed to us talking instead of messaging so we could masturbate and describe to each other what we were doing. Of course, she really didn't need to describe anything because I was watching her through the telescope but it was a huge turn on to watch and hear what she was doing at the same time.

The next Friday night when we chatted, Claire told me her roommate was going to be away for the weekend and did I want to get together again. That got an immediate "YES!" from me and a quick 'kiss' emoji back from her.

We both had some things that needed doing so we weren't able to get together until early afternoon but when I got there, she was waiting for me wearing a long t-shirt but I could easily see her nipples through it so I suspected she had nothing on under it. She suggested we sit on the couch and watch videos and I wasn't really surprised when the ones she brought up all had some sort of anal play in them. We kissed as we watched and soon were touching and teasing each other. It wasn't long before her t-shirt was off as was my shirt and shorts and we were heavily making out on the couch. When one of the videos had ended and we were looking for another one, Claire said, "Deb told me something else you said when you were with her."

"What was that?"

"Well, apparently you said 'a finger or something' when you were talking to her. Does that mean you've used something other than fingers in your ass?"

There wasn't much sense in denying it so I simply said, "Yes"

That got a very sexy grin from her before she said, "So do I! How about we take this to the bedroom?"

I was good with that and after making out there for a few more minutes, she said, "Remember last time when we watched each other finger our asses?"

When I nodded, she grinned and without saying anything else, she grabbed two medium size vibrators and some lube from the drawer and handed me one.

"If you're not comfortable enough, you don't have to but I'm going to use this one in my ass and I'd love to see you do the same."

I'm wasn't sure how many times I'd jacked off, thinking about doing exactly that while a woman watched but now that it was going to get real, I wasn't sure if I could go through with it or not. Without waiting for my reply, Claire added a bit of lube to her pucker and some to the vibrator before turning it on and slowly working the head in and out, going deeper and deeper each time. By the time she had the head inside her ass, I'd decided I might as well go for it and after a bit more lube for myself, I eased the head into my ass. When she saw what I was doing, she stopped long enough to just watch until I had the whole length buried in my ass and was slowly working it in and out.

That's when she returned to what she was doing and almost in sync, we were soon watching each other while we used a vibrator on ourselves. After a few minutes, I started slowly stroking my cock at the same time and she responded by starting to play with her pussy. So far, I was doing pretty well at holding back but I knew that eventually I'd be erupting from the pleasurable tingles I was feeling so I looked at her and asked if she'd like take over using the toy on me.

Her face lit up like a kid who just got what they wanted for Christmas and I got an immediate, "Yes, yes I would. How about you do me at the same time?"

That sounded good and after a bit of shuffling, we ended up in a separated '69' with her fucking my ass with the toy while I watched hers disappear into her own ass and then back out as I pushed and pulled. I could see how wet her pussy was and just couldn't resist moving my head a bit further forward so I could lick her clit and then down the whole length of her pussy. Feeling my tongue on and in her pussy prompted her to move so she could take my cock into her mouth. Oh, the number of times I'd laid on my bed and stroked my cock with one hand while I used a toy on my ass with the other, pretending a woman was sucking me and fucking my ass at the same time and now it was actually happening.

I was quickly reaching the end and usually I could feel it building and know exactly when I was going to cum but this time I went from "I'm close" to " cumming" in less than a second and then I was emptying myself into Claire's mouth. I don't know if she was already at the point of cumming or if my shooting into her mouth put her over the edge but right after I heard, "Oh yes!" I felt two distinct squirts from her pussy hit my face as she erupted in an orgasm of her own. I'm not really sure who moved first but eventually we were laying together on the bed, facing each other, with our arms around each other so we could relax and just enjoy the feeling of coming down from an amazing orgasm each.

She was the first to say anything with, "Wow, I've wondered what doing something like that would feel like for a long time and now that I've done it, it was even better than I thought. How about you?"

"Definitely the same! You watching me was hot and when you took over that felt way better than when I do it by myself. Being able to do the same with you made it totally awesome."

After a few minutes, Claire whispered, "If I remember right, with a bit of 'assistance', you should be good to go again in a bit."

"Good memory!" was all I got out before I felt Claire's fingers wrapped around my semi hard cock then they were followed by her mouth.

Sure enough, her fingers and mouth did the trick and it wasn't long before I was hard again. Moving back up, we kissed while she kept stroking my cock. She had a very sensual touch and while I'd have enjoyed her stroking me until I came, she had other ideas. Leaning close, she whispered, "Remember last time when I got you hard again and I rode you until we both came?"

As she talked, she was shifting to straddle my crotch and just as she started to lower herself, she finished with, "Well today I thought we could see how your feel in my ass instead."

Between the lube and the vibrator, she was already slick and open so my cock slid in much easier than I was expecting. Until you've actually had your cock in someone's ass, you really can't describe it. When it first slid in, I could feel her pucker opening to let me past and just like when I used a toy on myself, a couple of inches later, I could feel a second, tighter ring of muscle slowly let me in. From there, her ass was definitely tighter than any pussy I'd been in but at the same time other than feeling the two rings of muscle gripping my cock, the rest of her felt more 'open'. When she'd lowered herself fully onto my cock, she said, "You're a bit bigger than the vibrator but you're softer than the plastic and it feels great!"

Then she lifted back up and just when I thought I was going to pop out, she lowered back down again and I could feel both rings of muscle open to accept my cock again. As she found the speed and depth that felt best for her, I was busy teasing her nipples, rubbing her clit and fingering her pussy as best as I could. I was quite surprised when I heard her say, "Yours is the first real cock I've ever had in my ass and I love it!"