Boarding with Linda

Note: If you haven't already, read Chapters 01 - 12 of Boarding with Linda, which are prequels to this story.

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I experienced a lot of variety even within just the first six months or so of living in Linda's basement: blonds and brunettes, white, black and Filipino, big boobs and small boobs, curvy bodies and toned bodies. There was one thing for sure that I hadn't done, though; most of the women had been single like me and, although I'd been with a few divorced women, I'd never been with a married woman. It definitely wasn't a goal of mine, especially given that most of Linda's friends were single. Even sneaking around with Irene at first had been a lot more complicated than most of the experiences I was typically having. Since I was getting plenty of sex and there weren't really any married women in the picture anyway, hooking up with a married woman just wasn't something that I'd even considered.

As you may have figured out, I eventually had sex with a married woman but it may come as a surprise that it was orchestrated by Linda. She was telling me one evening about having lunch with her friend, Emily, who I had also known back when we all went to high school together. In fact, I had actually known Emily from when we'd been quite young because we'd gone to the same church. We had never really run in the same social circles, though, so we'd been more acquaintances than friends. Like Linda, she had married young and immediately got pregnant. Unlike Linda, though, she hadn't stopped at one and had remained married. She was now raising three kids but at least her husband was still in the picture.

Linda revealed that Emily, though happy in her marriage and with her kids and with her life choices, was feeling a bit overwhelmed, a bit underappreciated and quite a bit horny. With three kids, her sex life was definitely suffering. Without revealing our situation, Linda had told Emily that she knew somebody who could help her at least with relieving some of that pent up sexual frustration and, based on what she'd heard from some friends, he was quite adept at making a girl cum. She also assured Emily that this person could absolutely be discreet. She said that Emily seemed surprised by the suggestion but said that she'd need to think about it. I guess committing adultery wasn't something to be taken lightly, which is probably a good thing.

"So your friend tells you that, because she has three kids, she has no sex life and, rather than offering to watch her kids so she can have a date night with her husband, you instead pimp me out?" I asked, pretty amused and just good-naturedly giving her a hard time.

"First of all," she replied, "I have no desire to watch three little kids. Second, I can just see date night turning into a trip to Walmart and ending up with a quickie before they pick up the kids. At least with you I know that you'll make her a priority and make sure that she cums hard and cums a lot."

"This is true," I confirmed.

I hadn't even thought about Emily in years but confirmed that I'd be more than willing to help her out and, if she thought it would make a difference, she could tell Emily that it'd just be an old friend helping out an old friend; nothing more sordid than that. Of course, to frame it that way, she'd have to reveal who she was recommending that Emily have sex with but I suggested that maybe that would help her decide one way or the other, anyway. She decided that she'd follow up with Emily in a couple of days and, in the meantime, I went on social media to satisfy my curiosity. I remembered Emily mostly as being a skinny kid with really long hair but, naturally, she'd grown up quite a bit. She was a lot more curvy, presumably as a result of becoming a mom three times over, but this also meant that her tits were much more substantial than I remembered. I certainly didn't expect to have any reservations if she decided to go through with Linda's suggestion. Of course seeing pictures of her family did give me some minor reservations but she clearly was not as happy as those photos were suggesting so, if she felt like she needed something that I could provide, I wasn't going to second guess her decision.

Until she decided, though, there wasn't going to be anything to second guess anyway but, when Linda checked in with her, she'd made up her mind. She told Linda that she had decided to at least give it a try though she confessed that thinking of it as an old friend helping out an old friend helped her to rationalize her decision. Linda told me that Emily also seemed pleased when she revealed that I was the one who'd be taking care of her. They decided that she'd tell her family that she was having dinner at Linda's house and would be heading there right from work. Linda planned for her and Ashley to not be around so things weren't weird but I suggested that she have Emily knock then just come right in. I didn't think her husband would have any reason to be suspicious but, on the off chance that he was following her, it would be bad if he saw me answering the door to let her in.

I was far enough away from the door as she entered so that I couldn't be seen from outside but close enough so that I could admire her curvy figure as she entered. She was wearing a dress that complemented her curves and had buttons all the way up the front, which I knew I was going to enjoy unbuttoning. She locked the door behind her then crossed over toward me, not looking all that confident.

"Are you sure you want to do this?" she asked.

"Emily, we've known each other for so long," I said, earnestly, "that I think it's actually about time we did this."

I took her in my arms and she relaxed, wrapping her arms around my neck as I leaned down to kiss her. I could feel the blood flowing toward my cock as our tongues soon slipped into each other's mouths. I slipped my hands down to caress her ass but I didn't pull her against my stiffening cock just yet as we still needed to head downstairs. After a few minutes of highly enjoyable making out, we parted, looking into each other's eyes and smiling, then I took her by the hand and led her to the stairs. I headed down before her to lead the way and, once we were in my space, I just let her look around and take it all in. My cameras were all recording so it didn't matter where we started but I did have a basic plan and it seemed like she'd be looking to me to take the lead.

Once she appeared to be done exploring, I took her in my arms again and we resumed making out while I caressed her ass some more. She seemed to be relaxing even more so I was also hoping that she was getting worked up because I certainly was. I finally broke off our kiss and began to unbutton her dress, figuring we didn't have unlimited time and wanting to continue moving things along. My cock was growing even stiffer as first her bra and her significant cleavage were revealed then her matching panties. Since the buttons went all the way down to the hem of her dress, I ended up dropping to my knees to continue unbuttoning then I pulled her dress open and admired her figure.

"Oh yeah," I said, enthusiastically while gazing upon her appreciatively. Again, I knew we didn't have the time for me to just sit there staring at her so, as I was getting up again, I kissed her hips and abdomen then caressed her boobs through her bra while bringing my lips to hers again. She was definitely even more relaxed and completely into it by this point, which she made even more clear when she pulled her lips from mine.

"Oh my god," she said, "you've got me so worked up."

"The feeling is mutual," I said, taking her hand and placing it against the bulge in my shorts.

"I did that to you?" she said, sounding incredulous, "Can I take it out?"

She was already unbuttoning my shorts before I responded and, once they hit my ankles, I stepped out of them while she massaged the tented-out front of my briefs. She was quickly working my briefs down so that my rigid tool sprung out then she gently gripped it, slowly stroking it. She looked behind her then backed up, pulling me along by my tool, until she could sit on the end of my bed. I managed to ditch my underwear without tripping over it and, as she sat before me with her dress open but still in her own underwear, she held the base of my cock and engulfed it in her mouth. I moaned as her warm, wet mouth slid along my shaft and she gently pumped the base while also cupping my balls. Looking down, the bottom of my shirt was slightly blocking my view of her so I went ahead and pulled it up over my head and cast it aside. With my view of her efforts no longer obscured, I was watching as my cock repeatedly disappeared into her mouth, which was highly arousing.

She left nothing to be desired when it came to sucking cock and seemed pretty enthusiastic about it. I didn't know whether her enthusiasm came from just the overall enjoyment of sucking cock or if, with three kids around, she just hadn't had a chance to engage in it for a while. Either way, I was certainly enjoying her skills while thinking that she had to be getting incredibly wet just as I'd gotten incredibly hard. I knew if I just enjoyed her skillful blowjob and blew my load down her throat, I could then indulge in eating her pussy until I was recovered enough to fuck her, however long that took. I didn't try to hold back at all and just focused on enjoying the pleasure her mouth was providing.

My basic plan definitely had not involved me cumming first but I was nothing if not flexible. I had figured with her being pretty pent up that me going down on her and making sure she had a highly pleasurable orgasm or several first was a given. I liked that she had taken charge instead of continuing to have me lead because it appeared to me that it was driven by her desire to suck my cock rather than a desire to please me. Tonight was supposed to be about her so, if sucking my cock and swallowing my load was part of what was going to make her happy, I was all for it. Of course I was letting her know verbally how much I was enjoying her cocksucking just in case it wasn't obvious by how thick and hard my cock was.

As I was getting closer to cumming due to her skillful cocksucking, my cock was actually becoming even thicker but she didn't appear to be affected. She just continued gently pumping the base while taking as much of my length as she could into her hot mouth. Even when I started spewing with a grunt, she just swallowed down my load while continuing to suck me off. She didn't release my cock from her mouth until I was completely spent, then just smiled up at me, looking the happiest she had since she'd arrived.

"That was so amazing," I assured her as I knelt down. Now that I'd cum, I was eager to help her do the same. I pushed her dress off of her shoulders then fondled her big tits through her bra, feeling her hard nipples pressing outward. Reaching behind her, I unfastened her bra then watched her tits being revealed as I slid it down her arms. They weren't as big as Linda's but they would be big enough for me to lay my cock between them and fuck them. After casting her bra aside, I first fondled the bare flesh then lowered my head to lick and suck her hard nipples while she moaned in response. I knew this was just getting her even more fired up so I didn't linger too long because I was ready to devour her pussy, which I assumed was going to be incredibly juicy.

When I started to slide her panties down, she lifted her ass up off of my bed to make it easier for me. Her light brown bush was nicely groomed which made me wonder if that was something she could generally find the time for or if Linda had let her know what I liked. Once I had her panties off, she parted her legs and leaned back while I lowered my face toward her pussy. I ran my tongue along her slit, tasting the pungent juices she was abundantly producing and making her moan. Glancing up along her body as I lapped at her pussy, I could feel the blood already returning to my spent cock and knew that recovery definitely wouldn't be an issue. I also didn't expect that making her cum would be an issue but I was going to try to draw out the pleasure as much as I could without it feeling to her like I was denying her an orgasm.

I licked her slit for a bit longer before slipping a finger into her as I licked and sucked her clit. I followed the first finger with a second and, thanks to how wet she was, easily pumped them in and out as she began moaning louder and longer. When she reached down to hold my head, I glanced up again to see that her tits were squeezed between her arms, which only confirmed to me that I'd be laying my cock between them. She was rocking her hips rhythmically toward my face and clearly already building toward an orgasm. Her pussy was becoming even hotter and wetter the longer I was eating her and, as I thought about slipping my cock into her, it was stiffening even more. I definitely hadn't been getting bored with eating Linda's or any of her other friends' pussies, but it was always enjoyable to have a new one to taste.

I felt like I was staying on the right side of the line between drawing out her pleasure and denying her relief. She was gradually tensing up as she was getting closer to cumming and, although I was not necessarily ready to be done eating her pussy, I did want to make sure that her orgasm was the most pleasurable that I could provide. I'd figured that, if I wasn't quite recovered from her awesome blowjob yet, I'd just continue to eat her to another orgasm but my cock was nearly at full rigidity when she started to arch her back while forcing her pussy toward my face. It sounded as though she briefly held her breath before she let out a cry as her body went limp and she started shaking. I didn't let up in what I was doing, hoping to continue providing her pleasure, and it appeared that her orgasm was not only long but intensely pleasurable as well.

When she finally went still and silent, I straightened up on my knees and slipped my fingers from her pussy. As I gazed over her naked body while she was recovering, I sucked her juices off of my fingers while my cock continued to grow even stiffer. I stood up, in part to get a better view of her body, inspiring her to open her eyes, which went wide as she noticed that my cock was about ready to go again. She sat up and briefly stroked it, making it even thicker, then I moved past her and crawled onto my bed, lying on my back in the middle of it with my cock standing straight up. She turned and followed me, her big tits swinging, pausing to briefly engulf my cock in her mouth again before straddling me. As she grabbed my cock and guided it toward her pussy, I was gazing at her body while reaching up to fondle her tits.

We both moaned as she lowered herself onto my stiff cock then she sat there for a moment before beginning to move up and down. Her hot, wet pussy felt outstanding as it slid up and down my cock so I was glad that I'd cum once already because I knew it would aid my staying power and I wanted to be able to enjoy fucking her for a good long time. I was hoping for the converse reaction with her orgasms, that each subsequent one would be easier to achieve. While I definitely wanted to cum a few more times with her, I really wanted her to cum a lot more times. In this instance, it wasn't even about it making her more likely to return as it was about making up for all the orgasms she'd been missing out on since having kids. Based on the sounds she was making and the expression on her face, she appeared to be on her way to another orgasm already.

As she was riding me harder and faster, her tits were bouncing so I moved my hands away from them and around to caress her ass so that I could watch them. It was nearly hypnotizing to watch them moving up and down as she was riding my cock but it wasn't enough to distract me from the pleasure I was feeling as her pussy continued to become even hotter and wetter the longer she was riding me. I pushed up into her each time she dropped down so that she'd receive the full length of my cock and maximum penetration. Her moans were getting louder and longer as she was continuing to increase her pace so I knew it wouldn't be much longer before she experienced another orgasm. As I was running my hands over her ass while watching her tits, I was thinking that I might switch things up once she'd cum so that I could run my hands over her tits while watching her ass. I had a good feeling that there would be a bit of jiggle in it.

She finally dropped down onto my cock and went momentarily silent before gasping as her body started to shake. Since they'd stopped bouncing, I brought my hands back around to fondle her tits again. I don't know if caressing her hard nipples made her orgasm any more pleasurable but I was sure that it couldn't hurt. Aside from that, I just lay there and waited as she was cumming with my rigid cock still embedded deep inside her. Glancing up at her face, she appeared to be very content, smiling with her eyes closed. Even when it seemed as though her orgasm had run its course, she remained there sitting on my cock. I was perfectly content to lie there fondling her big titties as she was recovering so I just waited her out. When she finally opened her eyes, she smiled down at me, looking just a little dazed.

"I needed that so badly," she said, breathlessly, "Thank you."

"It was my pleasure," I assured her then I had her move off next to me, going from keeling to all-fours. I got up and moved around behind her, running my hands over her ass before guiding my still throbbing cock back into her hot, wet pussy from behind. We both moaned again as I slid in until my hips were touching her ass. Holding her waist, I started to slowly slide in and out, relishing the pleasurable feeling as she dropped her head to the bedspread and reached under herself to caress her clit. I suspected that she was probably used to caressing her clit to get herself off by this point so I figured that anything she could do to increase her pleasure was a good idea. Once we had a good rhythm going, I watched the anticipated jiggle of her ass each time my hips tapped against it before reaching forward to cup her swinging tits.

It felt as though my cock became even stiffer as I was fondling her tits and it seemed like she felt it, too, because she let out a louder, longer moan and her pussy actually felt a bit more slick. I continued to fuck her, gradually picking up the pace, while enjoying the feel of the soft, smooth flesh of her big tits in my hands. As her moaning became continuously louder and longer, though, I wound up straightening up and holding her waist again so that I could be sure I was giving her the full length of my hard cock with each thrust. Her ass was jiggling more as my hips were smacking into it repeatedly so my focus was entirely on watching that. Even as she let out a cry and her body started shaking, I continued to fuck her while staring at her ass.

Once she'd gone silent and still, I stopped and slipped my cock out of her. I had her roll onto her back then straddled her and lay my cock between her tits. She brought her tits together, denying me the opportunity to resume fondling them, but I was okay with that because it felt so incredible to slide my cock between them that I wanted to focus entirely on that. Holding onto my headboard, I slowly slid my cock against the soft, smooth flesh of her tits while looking down at her large areolas and hard nipples. Her tits were pretty awesome and I'd been fortunate enough to experience a lot of awesome tits since I'd moved into this room. Even given the number of other young ladies that had made themselves available to me for sex, I was actually hoping at this point that I'd get to see Emily again after this. I didn't want to come between her and her family, but I did want to continue helping her get the attention she needed until that could be resumed at home.