Boarding with Linda

Note: If you haven't already, read Chapters 01 - 15 of Boarding with Linda, which are prequels to this story.

I ended up living in Linda's basement and experiencing so many new sexual partners, including Linda, because my roommate, Rob, had proposed to his girlfriend. Naturally, when he asked me to be a part of his wedding party, I didn't even need to think about it. It wasn't just because he was indirectly responsible for such a vast improvement in my life; he was also one of my best friends. Jim was also a groomsman along with a couple of other guys. His fiancé was having her sister, his two sisters and a friend as her bridesmaids. I was paired in the wedding party with Rob's oldest sister, Kathy, who was only three years older than us. I was happy with this arrangement because I'd crushed on her back when we were in high school and she was in college. He was probably aware of that and had set this up as a favor to me, though I'm sure he wasn't expecting it to lead to anything and just figured I'd be happy for the couple of days that I'd be spending with her.

After the wedding ceremony, and all of the subsequent obligatory photos, the venue where the reception was being held had a private room for the wedding party so that we could have something to eat and something to drink while waiting for all of the guests to arrive and get settled. As we were hanging out, the topic of my living arrangements at Linda's house came up along with the work Jim had done to get my living space set up. As always, there were a lot of questions so I was used to answering most of them and generally steered the discussion back to Jim's outstanding work and Linda's generosity in providing a place for me to live. Naturally, there were a few jokes about what services I was performing for Linda in lieu of paying rent but only Jim knew that I was actually involved in a sexual relationship with her, as was he.

Since we were sitting together and danced together during the reception, Kathy asked a few additional random questions during the course of the evening, but it really did just seem to be curiosity. Since I knew that she passed through our hometown, where Linda and I still lived, on her way between work and her home, I invited her to stop by one day after work to check it out and satisfy her curiosity. If you are wondering whether I was hoping that her visiting would lead to an opportunity to get her naked then I'll have to assume that this is the first of my stories about boarding with Linda that you're reading. I was very hopeful that, if she was interested enough in my living arrangements to come over and check them out, that she might also be interested in feeling my hands on her big boobs, feeling my tongue on her clit and feeling my stiff cock sliding in and out of her pussy.

Linda was a guest at the wedding as well so she had the opportunity to give her two cents on our living arrangements to the curious. She was also open to having Kathy come visit us and check things out but she knew me well enough to be fully aware that there was also a secondary motive for me. Fortunately, she was not jealous or possessive and had even revealed that she got pretty fired up when she was aware of some of the happenings in my living space. She was definitely onboard to help make my desire to be with Kathy come to fruition. Kathy and I exchanged contact information before the end of the night and ultimately came up with a day that worked for her to swing by for a visit on her way home from work. Linda was there, too, the day Kathy came by so we all chatted for a bit upstairs before just the two of us headed downstairs for the tour.

Kathy worked in a bank so she was dressed in a skirt and blouse with a jacket over it, looking very professional. I pointed out a few things and reminded her of some of what we'd talked about before and during the wedding reception then invited her to just look around. I sat on my couch and watched as she made her way around the room. I was feeling hopeful, so I went ahead and turned on the cameras as I was sitting there. Even if I only ended up with footage of Kathy fully dressed, she was still looking really good.

"This is a lot nicer than I was expecting," she finally said, "I'm really impressed. When someone says that they're living in a basement, this isn't what would typically come to mind."

"Jim is a very talented contractor," I replied, "I give him all the credit for coming up with and building everything you see."

"What about privacy?" she asked, "You don't have any issues with Linda being right upstairs."

"She's very respectful of my privacy," I replied, "Not only do I have the separate entrance, so I don't have to walk my guests through the upstairs, but if that door from the rest of the basement is closed, she just assumes that I don't want to be disturbed."

Kathy walked over to that door, closed and locked it, then sat beside me on the couch. She leaned in to kiss me so we were quickly in each other's arms and making out. I brought a hand up to fondle her big boobs through her blouse and bra so she dropped her hand down to caress my stiff cock through my shorts. After a few very enjoyable minutes, she stopped and stood up.

"I want to show you something," she said, then hiked up the hem of her skirt to show that her stockings were clipped to garters which were attached to a garter belt, "I put these on this morning knowing I'd be coming over here and hoping that I'd get the opportunity to show them to you."

She was tall with long legs to begin with but seeing tops of her stockings and the garters made her legs look even longer. Her panties also matched the garter belt so I was assuming that her bra probably did, too, and I was feeling more confident that I'd be confirming that. Without letting her skirt drop down again, she knelt before me and was immediately working on getting my shorts opened. I lifted my ass up off the couch so that she could slide my shorts and briefs down while my stiff cock sprung out. She gripped it gently and briefly pumped it before lowering her head and taking it in her mouth. I moaned as the warmth of her mouth engulfed my tool and her lips started to slide up and down my shaft. I'm not sure how I didn't immediately begin to spew, especially since I was also watching as my cock disappeared repeatedly into her mouth.

Kathy and I had always flirted but nothing had ever happened between us before this. I don't know if it was just the time spent together at the wedding and the rehearsal and the reception or if, like me, she'd had thoughts about this before but had never found the right time until now. Either way, I was happy that things were going this way and that she had initiated it so I knew she was totally into it. She was proving to be a skilled cocksucker, not just by the amount of pleasure that I was feeling, but also because she was somehow managing to draw out that pleasure much longer than I'd have expected to be able to last. It wasn't like I was trying to hold back, although the longer this blowjob lasted, the happier I was going to be. I was just relaxing and enjoying both the pleasure she was providing and the view as my cock disappeared repeatedly into her mouth.

Regardless of her skill for drawing out the pleasure, there was a point where nothing could stop my orgasm from building and I was okay with that. I was confident that this wouldn't be my only opportunity and that we were just getting started so there would be plenty of other enjoyable things to experience. Even as my cock was becoming thicker as I got closer to cumming, she was unfazed and just continued to suck me off. When I exploded into her mouth with a grunt, she swallowed my load without even hesitating then continued to milk every drop of cum out of me. Only once I was completely spent did she release my softening cock from her mouth then she sat back on her heels.

"That was so amazing," I finally said, "but you have to let me take care of you now."

"I'd have no problem with that," she confirmed. I sat up and removed my shirt since it was the last thing I was wearing then we both stood. I helped her out of her jacket, set it aside, then reached behind her to unhook and unzip her skirt. I hunkered down to work it over her hips and down her legs then she stepped out of it and I set that aside, too. As I stood again, I was unbuttoning her blouse, revealing that her bra did, in fact, match her panties and garter belt.

"My god, you are so fucking sexy," I said as I removed her blouse and put that with her jacket and skirt. I had to take a moment to just admire her in just her lingerie while making sure that the cameras were getting some good footage. She seemed pleased by the attention and that her outfit was having what was presumably the desired effect. I fondled her big boobs through her bra, caressed her ass through her panties then ran my fingers up along her slit, through her panties as well. She moaned softly so I figured I'd better get to taking care of her and had her sit on the couch where I'd been. I took her place, kneeling in front of her, and parted her legs then pulled her panties aside. I was planning to take them off at some point, as well as her bra, but I wanted to keep all of that sexy lingerie on her for the moment.

I lowered my head and ran my tongue along her slit, which caused her to suck in her breath then let out a moan. I may have mentioned previously how much I enjoy eating pussy, especially when it is a pussy I've never eaten before, but when you add in that it is also someone whose pussy I've been wanting to eat, it was like Christmas Day for me, but with more nudity. I wanted to spend plenty of time relishing this opportunity while also drawing out the pleasure so that she enjoyed it enough to want to be back in this position with me. My skills had been honed with all of the experience I'd gained since moving in with Linda so I was implementing every technique I knew to enhance Kathy's pleasure. I'd slipped a finger into her and was licking and sucking her clit while sliding it in and out, making her moan louder and longer, which I knew was a very positive sign.

She leaned back and was running her fingers through my hair so I glanced up to see her big boobs, still in her bra, squeezed together and practically spilling out. I was eager to set them free and fondle them, among other things, but this had been such a long time in coming that I wasn't going to rush any part of it. Likewise, I was aware that she had what appeared to be a well-groomed, dark brown bush but I wouldn't get a good look at it until I removed her panties, which I obviously still planned to do. In the meantime, I continued to lick and suck her clit while sliding my finger in and out of her snug, slippery pussy, working on providing the highest level of pleasure while savoring the opportunity to be doing so.

Her moaning was getting even louder and longer and she was beginning tense up some so I could tell that she was at least building toward an orgasm, though I didn't have an idea of just how close it was. Despite all of my recent experience with eating pussy, each partner was different in so many ways that it was never an exact science, nor would I want it to be. One of the things with continuing to hone my skills was learning to be flexible and roll with the changes if something wasn't working the way it had for somebody else. I did have a better handle on the fine line between drawing out the pleasure and denying the relief of an orgasm. I don't feel like there were many times that I'd crossed that line, if any, but there were probably times I got nervous about cutting it too close and had prematurely ceased trying to draw out the pleasure.

I wasn't aware of what Kathy's current situation was as far as if she had someone else taking care of her sexually but, if she'd been thinking about something like this potentially happening at least since she'd dressed that morning, it seemed reasonable that she'd be pretty fired up by the time it actually started happening. That being said, I hadn't wanted to just provide relief but extended pleasure as well, and when I felt like I'd successfully done that without crossing that fine line, I focused on getting her the rest of the way to an orgasm. Almost immediately, she was tensing up more and arching her back while her pussy was becoming even hotter and wetter, which made me even more eager to slip my cock into her.

She briefly went still and silent, then cried out as all of the tension left her body and she started shaking. I continued to devour her pussy even as it was flooded with additional lubrication that I briefly considered slurping up rather than more easily pumping my finger in and out. Her orgasm was long and appeared to be highly pleasurable so I kept up what I was doing since it had worked so well, only stopping once I was certain that she'd finished cumming. I slipped my finger out of her pussy and into my mouth to suck the juices off while straightening up and looking over her body. My cock was nearly rigid again by this point and I knew exactly what would get it the rest of the way to full rigidity.

Once she had recovered, I stood and helped her up as well. Reaching behind her, I unfastened a row of hooks on the back of her bra then stepped back as I slid it down her arms, revealing her big, beautiful boobs. They sloped down a bit under their own weight but mostly held up firmly even without the bra. Her areolas were large and her nipples thick and hard so, after briefly just staring at them, I dropped her bra and reached for them, running my hands over the soft, smooth flesh and her hard nipples as she sighed. When I lowered my head to lick and suck her nipples, she had her fingers in my hair again and was moaning softly. I was fully rigid by this point so I knew I could continue to play with her tits while we were fucking and took steps to get us there. I dropped down in front of her and slid her panties down, revealing a well-groomed, dark brown bush. As she stepped out of her panties, I planted kisses on her hips and stomach then stood again.

I was standing back far enough that I could admire how she looked wearing just the garter belt and stockings then had her turn so that I could see her ass, which was incredibly sweet. Not wanting to wait any longer, I sat on the couch and had her straddle me, holding her waist to steady her as she reached down for my cock and lowered herself onto it. We both moaned as my stiff cock eased into her snug, slippery pussy while I moved my hands up from her waist to fondle her big titties again. She sat there on my cock for a moment before beginning to slowly move up and down, which felt absolutely amazing. Despite everything that had happened since I'd moved into Linda's basement, it was still nearly unbelievable that Kathy was mostly naked and riding my cock.

Once she had a rhythm going, she brought her lips to mine and we were soon making out while we were fucking. My hands remained on her tits for the moment because they were far surpassing any fantasy I'd ever had about fondling them. I was able to push up into her each time she dropped down, making sure she was getting the full length of my cock, while our tongues were exploring each other's mouths. Between the regular sex and the earlier orgasm, my staying power was in good shape so I could focus on the pleasure I was feeling rather than trying to distract myself to last longer. Feeling her snug, slippery pussy moving up and down my cock, I definitely was glad that I didn't have to think about something else though I did want to experience that pleasure for as long as possible. Of course, if she ended up having a quick orgasm then wanted to switch things up, I would be fine with that, too, since I still expected that I'd be enjoying the pleasure of fucking her.

We had a good rhythm going pretty quickly but it wasn't long before she was riding me a bit harder and a bit faster. We continued to make out for as long as we could but she eventually pulled her mouth away from mine so that she could let out some long moans, though she did manage to keep her volume down. She was clearly building up to another orgasm, not just based on this, but I could also feel her pussy becoming even hotter and wetter.

She finally dropped down onto my cock and just sat there, briefly going silent as well, then let out a soft cry as her body started shaking. I continued to caress her succulent boobs while she was cumming since there wasn't much else I could do. It was another long and apparently intensely pleasurable orgasm so I was pleased to have helped her to achieve it. When she finished cumming, she remained seated on my cock as she recovered then brought her lips to mine and we kissed again. Before she resumed riding me, however, I had her climb off of my cock and get on all-fours beside me. I knelt behind her and guided my cock back into her hot, wet pussy from behind.

We both moaned as I slipped all the way in until my hips were touching her ass. I held her hips as I began to slowly slide in and out, once again savoring the feel of her snug, slippery pussy gripping my stiff cock. Looking down, I admired her ass while feeling grateful for the opportunity to do so. Once I had a good, steady pace going, I slipped my hands forward and cupped her boobs. As I felt the soft, smooth flesh and her hard nipples, it seemed like my cock became even harder and, based on the moan that she let out at the same time, she clearly felt it, as well. I noticed that she reached one hand back under herself and assumed it was to caress her clit while I was fucking her. I was pleased that she was being proactive about her own pleasure.

It felt like we were really in sync, with her pushing back and me pushing in while I fondled her boobs and she caressed her clit. I still wasn't feeling my own orgasm beginning to build, despite how incredible it felt as I was fucking her. I attributed that entirely to being a benefit of having regular sex so that I wasn't so pent up.

She ended up pushing back a bit harder and a bit faster the longer we were fucking which eventually triggered me to straighten up and take her by the hips again. I left the pace to her but made sure that, each time she pushed back, I gave a good thrust so that she was getting the full length of my stiff cock. She was moaning more continuously and I could feel her pussy becoming even hotter and wetter and it felt outstanding. I could have enjoyed it for much longer but she ultimately ended up pushing back and holding there so I just made sure I was fully embedded inside her. A moment later, she let out a cry and started shaking. Knowing that she was likely being flooded with even more lubrication, I couldn't resist sliding my cock in and out of her as she was cumming and I'm sure she didn't mind.

After another long and apparently highly pleasurable orgasm, I ended up slipping my cock out of her and having her lie on her back. I moved up and straddled her ribs, laying my stiff cock between her big boobs. Taking one in each hand, I brought them together and began to slide my cock against the soft, smooth flesh. She was watching as my cockhead repeatedly peeked out of her cleavage, waiting for me to spew. I knew she wasn't getting much from me fucking her tits but I would have been happy to fuck those big beauties for the rest of the night. I felt my orgasm beginning to build due to feel of the soft, smooth flesh sliding against my stiff cock so I just savored the increasing level of pleasure. I loved the feel of her big boobs in my hands, too, so that further boosted my enjoyment. As my cock swelled even more when my orgasm was imminent, I most definitely was not disappointed to be close to finishing up since I was expecting that this was not going to be my only opportunity to enjoy having my cock between her big boobs. I maintained the slow pace, both for my enjoyment and so I didn't cause any discomfort for her.