FWB Ch. 03: Colleen

Note: If you haven't already, read FWB1: Kaylee & FWB2: Kaylee, which are prequels to this story.

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Kaylee and I definitely made the most of every opportunity that summer to fuck and otherwise pleasure each other. We both had jobs, so we weren't always together, and we each had other friends, though we tried to include each other with them so no opportunities were missed. A lot of people assumed we were dating but a lot also just assumed that, since we'd both be starting college at the end of the summer, we were just friends with benefits. The latter were, of course, correct and, despite how intimate we were, neither of us was interested in establishing a committed relationship. As horny and as sexual as we both were, there was no way that, once she went off to school and I started school locally, we'd be able to wait to see each other again for sex. I think we were both expecting that we'd meet somebody new once school started, though we'd see each other on breaks and resume fucking then. We didn't talk about it because we were living in the moment but, as the summer was starting to wane, it was apparently on Kaylee's mind. It was shortly before she would be leaving for school when she finally brought it up.

"I've been thinking and I don't want you to take this the wrong way," she started, "because I know with your skills you will have no problem finding somebody else to be with once I'm gone. I also know, though, that girls can be weird and you might find yourself dealing with a whackjob instead of getting a blowjob. So I want to put this out there for your consideration: I've got a friend who has a little bit of experience but who wants more and I can't think of a better person to get experience with than you. She doesn't have a friend with benefits and you're going to have a void in that area, so it just seemed to make sense to hook the two of you up."

"I don't know what to say; that's very sweet of you," I replied, "I would definitely feel more comfortable being with somebody who's been pre-screened by you and, though I think you overstate my skills, I wouldn't turn down the opportunity to help somebody get more experience."

"You don't need to know who it is first?" she asked.

"No," I replied, "I trust you and know you wouldn't suggest this with somebody I wouldn't be compatible with. Of course, I'm interested in who it is but finding out won't make me change my mind."

"Okay," she said, "it's Colleen."

"Really?" I replied, feeling relief, "I wouldn't have thought she'd have any trouble finding somebody who'd want to get naked with her."

"Well, like I said," she went on, "she has some experience but let's just say it hasn't all been good experience."

I had met Colleen a few times and would absolutely have no issue with her stepping in to fill the void that would be created by Kaylee's departure. She was cute with dark blonde hair and had more curves than Kaylee. She also had some serious tits. She didn't flaunt them but I'd seen a few pictures through Kaylee's social media accounts where they were pretty well on display. I wondered if the bad experiences had been with guys solely focused on getting their hands on her tits. I couldn't blame them but I would certainly be interested in the rest of her body, as well, and the pleasure that I could provide her. As much as Kaylee talked up my "skills," she'd definitely helped me refine them over the past few months so it would be interesting to put them to the test with somebody else.

It turned out that Colleen would also be going to school locally and living at home, though we weren't attending the same school. The last time I saw Kaylee before she left for school, she gave me an envelope which I was to open after we'd parted. It contained a note and a key, one of which explained the other. She told me that, the morning of her departure, I was to take the key to her house at 10am sharp. She and her parents would be gone by then and the house would be empty for a few days so Colleen would be meeting me there with another key. One of us would have the door key and the other would have the deadbolt. I'd wondered how she was going to arrange for us to get together and this worked well so that we'd have time and a safe location to get things started.

We arrived pretty close to the same time that morning and I was pretty excited about what the day promised. I was hoping that she was likewise excited and not nervous. Hopefully Kaylee would have put her mind at ease as much as possible. She was wearing a sundress and, as usual, her big boobs were not fully on display, though I knew that would change once we were inside.

"Hi," she said, with a smile.

"Hi," I replied.

"I almost feel like I should thank you," she said.

"I'd wait on that," I replied, "because you may end up wanting to take it back."

She burst out laughing which caused me to smile.

"Oh my God," she said, "I so needed that."

"Okay, so, the ice is broken," I replied, "I think we should continue inside. I'm sure any nosy neighbors will recognize both of us and both of our cars but we shouldn't give them any reason to think we're here for anything more than checking on the house."

"Agreed," she said, "got your key?"

I showed her that I did and we headed up the driveway to the front door. We managed to get the right keys in the right locks on the first try and were soon relocking the door from the inside. We headed up the stairs immediately since Kaylee had indicated for us to use her bedroom, though she'd specifically asked us not to leave any evidence, including stains on her bedclothes that might lead to questions from her parents. Once inside the bedroom, I took her in my arms in the middle of the room and brought my lips to hers. Kissing quickly progressed to making out as my hands slipped down to caress her ass and pull her against my stiffening cock. She was definitely a good kisser and her ass, which was much fuller than Kaylee's, felt nice.

Not unlike my first night with Kaylee in that same location, I picked Colleen up and carried her to the bed where, also not unlike my first night with Kaylee in that same location, I planned to push up her dress and eat her pussy. My staying power was probably a little better after all the sex Kaylee and I'd had during the previous months, but I still knew I would feel more comfortable making her cum at least once just in case. I lay her in the middle of the bed and, since we both knew why we were here, I didn't go back to making out with her or dry humping her as Kaylee and I had done. Instead, kneeling between her legs, I slid the hem of her skirt up along her thighs as I lowered my head. As her panties came into view, I was kissing her soft, smooth inner thighs, working my way closer to her pussy. I pushed the hem all the way up below her succulent tits and kissed her abdomen as I caress the front of her panties before starting to slide them down. She raised her ass to allow me to do this more easily and I soon got a nice look at her trim, dark blonde bush. I don't know if Kaylee had shared the things she'd learned that I like with Colleen but her bush looked just perfect to me.

As I cast her panties aside, I was moving my face back toward her pussy, admiring how nice it looked as I did. I suspected that I was going to enjoy seeing her naked almost as much as I was going to enjoy fucking her. I ran my tongue along her slit, tasting the copious juices she was producing while causing her to moan. I'd been eating Kaylee's pussy all summer so I definitely detected a slightly different flavor as I lapped at Colleen's. It wasn't something I could necessarily pinpoint but it was noticeable. I may have lapped at her pussy a bit longer as I considered it, but then slipped a finger into her, finding her pussy as snug and as wet as Kaylee's had been. While I was making these comparisons in my mind, I had no intention of talking about any similarities or differences with either of them. They might decide to compare experiences, but I would leave that to them.

She was getting louder as I licked and sucked her clit while sliding my finger in and out of her pussy but obviously I had no idea how close she was to cumming. The fact that she was clearly feeling pleasure was enough for me, though; I was planning to eat her pussy until we were both satisfied, regardless of how long that took. I was relishing the opportunity to eat another pussy after a few months of enjoying only Kaylee's. It wasn't that I'd gotten bored with hers but a new pussy I'd never tasted before was always a treat and I always made the most of the opportunity. Of course, I made the most of every opportunity to eat a pussy. Colleen was definitely writhing more and getting louder the longer I was eating her. Her pussy was also becoming even wetter and more engorged. When she started tensing up and arching her back, I was pretty confident that she was on the verge of cumming. I didn't change my technique and just kept going until she finally went limp and her body started shaking.

I continued eating her through her orgasm and didn't let up once she'd finished. She didn't try to stop me and was soon writhing and moaning again. I'd historically had pretty good success with subsequent orgasms after the first one and wanted the first time I went down on her to be not only memorable but comparable to what had happened my first night with Kaylee, and not only for the sake of a future conversation between the two of them. It did take much less time to reach her second orgasm than it had her first and a few more after the second took about the same amount of time and effort. When I finally raised my head and slipped my fingers from her pussy into my mouth, it wasn't because I wasn't interested in continuing or my tongue was getting tired; I was more afraid, based on glancing up at her, that she was going to end up completely out of it and I still wanted to get her naked and fuck her.

I straightened up onto my knees, looking down on her expression as she seemed to be coming back to herself. I raised my shirt up and peeled it off, then cast it aside. Next, I started to unfasten my shorts but I knew I wouldn't be able to get them off while kneeling, so I flopped over onto the bed beside her. Before I pushed my shorts and underwear down, I remembered to grab my wallet and take out the condom inside it. As I was doing this, Colleen got up onto her knees, the hem of her sundress dropping down to cover her pussy. She helped me get my shorts and underwear down and off once I'd shoved my wallet back into the pocket. My cock was rigid and standing straight up but, instead of reaching for it or lowering her mouth toward it, she pulled her sundress up and over her head. It felt as though my cock became even harder as I stared at her wearing only her substantial bra. I tore the condom open and was rolling it on as she reached back to unfasten her bra. As she let it slide down her arms and her tits were exposed, I actually softly muttered, "Oh my."

I didn't want to be solely focused on her beautiful and considerable tits but they really just could not be ignored. I'd never seen a pair so big in person and was presumably as fascinated as any other guy who had seen them. As I was taking them all in, she moved over to straddle me and guided my cock toward her trim bush. We both moaned as she lowered herself onto my cock and I realized that her pussy was just as incredible as her tits. Knowing this, of course, did not stop me from reaching up to caress them, though I tried not to be completely ham-handed; my caresses were intended to provide some level of stimulation or pleasure to her. I'm sure there were guys who just wanted to grope or squeeze them, and I'm not saying that I didn't, but I was pretty fascinated by how soft and smooth they were, how big her areolas were and how thick her nipples were.

As she started riding me harder and her tits started bouncing, I moved my hands so I could watch them. I slipped my hands over her curvy waist and around to caress her ass while also pulling her down as I pushed my cock up into her. In spite of the condom and all the sex I'd been having with Kaylee all summer, my orgasm was building up more quickly than I'd hoped. Part of that, of course, was Colleen's hot, slick, snug pussy but part of it also was just being with somebody new and being completely turned on by her. Since I'd successfully been able to make her cum numerous times with my tongue and finger, I was not feeling any stress about cumming quickly and knew I'd be able to spin it that she was just too sexy for me to be able to last that first time. Since she was controlling the pace, there wasn't much I could do to try to hold out longer, anyway, so I just enjoyed the building pleasure as her pussy moved up and down my tool while watching her titties bouncing.

Had I been in control of the pace, I'd probably have started fucking her harder and faster the closer I got to cumming. Since she didn't know how close I was, she didn't pick up the pace to where I would have set it so I was actually able to last a bit longer and enjoy a slightly slower build-up. Ultimately, though, my cock started swelling even more and, when I started spewing into the condom, I let out a soft cry because it felt so damn good. She continued riding me and, before I'd finished cumming, she dropped down onto my cock and sat there as her body started trembling and she let out a soft cry of her own. I was happy that she'd been able to cum again and was thinking that Kaylee was awesome for connecting the two of us. I knew I was going to enjoy being with Colleen and I suspected that she was feeling the same about being with me.

"I hope you don't mind that I'm not like Kaylee," she said as she climbed off of my shrinking cock and lay beside me, looking at the ceiling.

"In what way?" I asked, looking over at her.

"Well, I'm not exactly skinny," she said, looking at me almost apologetically.

"First of all," I started, "I love your figure, and not just your ginormous boobies. I'm actually glad you aren't built like she is because I'm not trying to replace Kaylee, and you shouldn't be, either. The only way I think it's important for you two to be alike is for you to like sex as much as she does."

"I now understand why she likes it as much as she does," she replied, "and I'm definitely a convert, too."

She went on to explain how her previous experiences hadn't been so great so she didn't really get all the fuss about it. She knew that Kaylee's hadn't been much better before I came along and she kind of didn't believe what Kaylee was telling her, that it could actually be that good. Now she understood, and we'd only just gotten started. I had gotten up as she'd been talking to strip off the condom and wrap it in the Kleenex I used to wipe off my cock. I set both where we'd remember to take them when we left.

"So you're saying you enjoyed it?" I asked as I returned to the bed and lay beside her.

"Enjoyed would be an understatement," she replied with a big smile.

"Well maybe we should do some more, then," I suggested and leaned closer to kiss her while running my hand along the curve of her waist. She was on her back and I was on my side so I ended up kissing my way down along her neck then down the slopes of her boobs which, despite their size, were still essentially pointing upwards. When I reached her nipples, I ran my tongue around her areolas and sucked her nipples, alternating from one to the other. I was also caressing the soft, smooth flesh but my hand gradually moved down over her stomach to her pussy. As I slipped my finger into her again, I wasn't sure if she was so wet again or so wet still. I alternated between pumping my finger in and out and lightly caressing her clit. When I went back to making out with her while still stimulating her pussy, she reached down to find that my cock was reviving rather nicely. Once she started stroking it, however, it revived a lot more quickly. It wasn't long before I was fully rigid once again. I was thinking about how, the first time I'd been in Kaylee's bed, I'd been able to make her cum just with my finger while she'd still been wearing her panties. I figured, if she'd told Colleen about that, I might as well just go ahead and show Colleen how I'd done it but it turned out that she had another idea.

"Did you bring another condom?" she finally asked, pulling her mouth from mine.

"Of course," I replied, "I was hoping you'd want to do it more than once."

"Kaylee said she left some condoms hidden for us, just in case," she said.

"Well let's use Kaylee's condoms, then," I replied, "and save mine for next time."

She got up and went to retrieve them from what turned out to be the same place Kaylee always kept her condoms stashed, on the shelf in her closet. I was sucking Colleen's flavor off of my fingers as I watched her walk over, her tits bouncing then her sweet ass aimed at me. She turned back with a strip of condoms and a smile as I continued to admire her body.

"You really have a fantastic ass," I said.

"Big boobs, fantastic ass and a hot pussy," she replied, "I'm a triple threat!"

She was laughing as she rejoined me on the bed but I totally agreed with her. Kneeling beside me, she opened a condom and rolled it onto my cock, her hand making sure that I was still fully rigid. I was pleasantly surprised when she got on all-fours beside me.

"You can admire my ass while you're fucking me," she said, "but do not even try to stick that in my ass, got it?"

"Absolutely," I replied, kissing her before I got up on my knees behind her. I did admire her ass and lowered my head to run my tongue along her slit again, causing her to moan. My cock was throbbing so I straightened up on my knees and guided it into her snug, slippery pussy, my moaning joining hers. She had her head resting on the comforter but it appeared that she'd slipped an arm under herself, presumably to reach back and stroke her clit. I held her waist as I slid my cock all the way into her, until my hips were pressed against her ass, then started to slowly fuck her. Once I had a rhythm going, I slid my hands down from her waist to caress her ass as my hips repeatedly bounced against it.

I'd fucked Kaylee from behind plenty of times, though only a few in this exact spot, but fucking Colleen felt entirely different. They both had really snug, really slippery, really hot pussies but Colleen had more ass to caress since she had more curves and she was also a bit taller than Kaylee, so the angle that my cock was sliding in and out was different. Of course, as I'd said, I wasn't looking to replace Kaylee with someone similar to her but I couldn't help make comparisons after having spent so much time with her over the previous few months. Nowhere in my comparisons was I considering quality, either; fucking both of them was absolutely exceptional and I appreciated the opportunity to be with Colleen now that Kaylee was away.

The longer I fucked her, the more she was pushing back against my incoming thrusts so, ultimately, I ended up letting her control the pace and was more just giving a slight push each time her ass hit my hips. I knew her tits were swinging so I reached forward to cup them, feeling her hard nipples against my palms while hefting their substantial weight. I didn't want to focus too much on her tits, since I assumed most guys did, but neither could I ignore them and, as I fondled the soft, smooth flesh, I knew I could not deny myself the pleasure of fucking them. I couldn't imagine she'd be put off by it, especially since I'd successfully helped her cum already and intended to at least once more before I moved on to doing that.

When it sounded like she was getting close to cumming again, based on the noises she was making, I straightened up again and held her waist while still leaving the pace to her. Her ass was smacking against my hips as she pushed back faster and harder and I loved seeing it jiggle each time. My own orgasm was building, as well, but I was pretty confident that she'd beat me to the punch. When she pushed back hard and just stayed there with my cock fully embedded in her, I felt her entire body start trembling as she did cum. This orgasm seemed to be just as long and intense as the previous ones so I was glad once again, as I had been with Kaylee, that she seemed to have no problems with cumming. They could claim all they wanted that it was because of me, but I knew that the credit was not fully mine.