Boarding with Linda

Disclaimer: This is a work of fiction concocted entirely within my imagination. Any resemblance to real people shouldn't be surprising since most of my stories are based on people I know. While I hope you enjoy this story and are compelled to provide feedback, I don't expect the subject matter will appeal to everyone who reads it. As such, I discourage venomous, nasty feedback full of violent wishes against essentially fictional characters in fictional situations. If this story does not appeal to you, there is undoubtedly one somewhere on Literotica that will, so your energy will be better spent on finding it rather than on vilifying me. Your opinions are welcome but your attacks are not.

Note: If you haven't already, read Chapters 01 - 11 of Boarding with Linda, which are prequels to this story. Also, this is basically the first piece of erotica I ever wrote for posting online. It has been modified just slightly to be included in this series and, even so, is still far from my best work.

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It had occurred to me more than once that, if it wasn't for my roommate, Rob, getting engaged and getting a place with his fiancé, I'd likely never have ended up moving into Linda's basement and getting all of the pussy that I could ever want. The two of them still came to most of Linda's parties and we also still hung out together plenty otherwise, so I made him well aware of how much action I was getting, though I didn't tell him about Linda or Irene. Of course he was jealous to some extent, but his fiancé, Dana, was really cool and they were really happy together, so I don't think he really gave it too much thought. I was really glad that they'd found each other and that things were going so well for them because, to be honest, I was really wondering if she was right for him in the beginning. I knew that she hadn't been faithful to him initially because she had offered herself to me and, of course, I had not turned her down.

I hadn't had any intentions of trying to fuck Dana when she and Rob first got together. She was curvy like Tara with a really nice set of tits but I'd just never really felt any particular attraction to her though certainly not because of her weight. Alcohol has a way of changing such things, though.

Going back a little farther, Rob and I had been friends for about ten years and roommates for just one when this all took place. He met his girlfriend, Dana, through her sister, Lori, who was involved with Jim before he and Irene got serious. They had been dating for about four months when this first incident occurred.

One weekend, Rob was out of town on a hunting trip. I assumed Dana would be spending the weekend at her house, where she lived with Lori and their mom, and I wouldn't be seeing her. Jim and I ended up going to a party just a few miles from Dana's house and after a night of carousing and numerous beers, Jim decided that he wanted to see Lori. He knew that there was little concern of Dana and Lori's mom being home since she was divorced but had a boyfriend that she spent most of her time (and nights) with. So, since Jim was my ride, I went along figuring I would do nothing more than bullshit with Dana while Jim and Lori got their rocks off. Lori and Dana were in bed when we got there, but got up and let us in with no complaints. During the requisite small talk before Jim and Lori took off, I excused myself to go upstairs to pee. The second floor was just the bathroom and two bedrooms (Lori and Dana shared one). After peeing, I looked into their bedroom and, realizing how drunk and tired I was, decided the hell with everyone else and crashed in what turned out to be Dana's bed.

I found out later that they began to wonder what had happened to me and when they found me sound asleep they all just decided to crash, too. I still am not sure why Dana didn't just sleep in her mom's bed; maybe she wanted something to happen or maybe she just felt comfortable enough with me and trusted me. Either way, I never felt her climb into bed, but awoke later to find her there. The bed was not very large and we were sleeping spoon fashion with me between her back and the wall. I innocently draped an arm over her just to give myself a bit more room and accidentally contacted one of her substantial bosoms. Instantly, her nipple reacted to my touch and feeling that, I couldn't help myself and started to caress it.

She didn't move or say anything as I went from caressing her hard nipple and cupping her entire breast. My cock was stiffening but, because I was still wearing jeans, she may not have felt it pressing against her ass. Since she hadn't reacted to my touch, I wasn't even sure if she was awake. When she finally rolled toward me, I thought she might be about to give me hell...until I felt her lips on mine. We slipped our tongues into each other's mouths as our hands roamed each other's bodies. Mine eventually returned to her breasts, this time beneath her nightshirt, after passing over her smooth thighs, panty-covered pussy and soft belly on the way up. I continued to play with her nipples while we made out, but eventually my hand headed south again, briefly caressing her pussy through the front of her panties before venturing inside.

She parted her thighs as my fingers passed through her closely cropped bush, over her clit and into her dripping pussy. I slipped a finger in and out of her, noting how hot and wet she was as well as that she was pretty snug. After a brief exploration, I concentrated on her clit, lightly running my finger over it. She was halfheartedly rubbing my cock through the front of my jeans, concentrating instead on the pleasure she was experiencing. She began to push her hips upward harder and pulled her mouth from mine as her breathing quickened. It seemed like she was struggling to keep from making too much noise, which I took as a good sign that she was building toward an orgasm. When I briefly slipped a finger back into her pussy again, I was surprised by how much wetter and more engorged it had become. It was pretty clear that she was right on the verge of cumming. I kept gently stroking her clit as her body tensed up until she suddenly went limp and her body was shaking. I didn't stop as she rode out what appeared to be a long and intense orgasm but, when she went still, I slipped my hand from her panties and went back to caressing her substantial tits.

Once she'd caught her breath, she whispered softly for me to go to the bathroom then meet her in her mom's room after. I kissed her and quickly left. After all that beer, my bladder needed relief anyway. I took my time peeing, washed up and even rinsed with some mouthwash before quietly heading to the other bedroom. There I found Dana waiting in the dim light with the sheets pulled up to her breasts, but obviously naked. I closed and locked the door then climbed on the queen-sized bed to make out with her and kiss and suck her milky white tits. She helped me out of my shirt, then rolled me onto my back and kissed her way down my chest while unfastening my jeans. As she slid my jeans and briefs over my hips, my cock sprung out only to be instantly engulfed in her warm, wet mouth. I kicked my jeans the rest of the way off while she grasped the base of my shaft and slid her mouth up and down. She was obviously skilled as she tongued my head and shaft and caressed my balls when she wasn't straight up sucking my cock. Even with all the alcohol in me, her expertise was just too much and I could feel my orgasm building much more quickly that I would have hoped. Since she had already cum, I could have been okay with cumming quickly but I was definitely into what was going on and didn't want it to end. Figuring I could spend a little more time exploring her curvy figure, I managed to just relax and enjoy the significant pleasure she was providing. It didn't take much longer before I was shooting my load down her throat. She swallowed every drop and only let my cock fall from her mouth once I was completely spent. She then made her way back upward where she kissed me hard before bringing her breasts to my face.

Again I licked and sucked her nipples while my hands roamed over her ass and underneath to her still wet pussy. I rolled her onto her back while still working on her tits, then began to kiss my way downward. After admiring her trim, brown bush (the carpet definitely didn't match the drapes), I buried my face between her thick thighs and ran my tongue up her slit. She was overflowing with pungent nectar, which I lapped up as she moaned softly. I slipped a finger into her while flicking my tongue over her clit which caused her to suck in her breath before continuing to moan. She held the back of my head and, as her orgasm was building, mashed my face into her pussy. I kept up licking and sucking her clit while fingering her until she once again started shaking as she experienced her second orgasm. When she went still, I crawled up and kissed her passionately. She reached under me and found my growing cock so she began to stroke it.

It didn't take much between her hand on my cock and her tongue in my mouth before I was ready for another round. Breaking off our kiss and moving back down between her legs, I grabbed her legs under the knees and lifted them until her knees touched her breasts. She guided my cock into her hot pussy and I immediately began fucking her hard and fast, my hips slapping against her ass. As much as the experience had me fired up, it didn't take long before I started to recall how tired I still was, especially given the late hour. I wouldn't say that I necessarily wanted to be finished fucking her but I wasn't sure how much stamina I'd have left. Dana was responding to my vigor with her own, raising her pussy to meet my incoming thrusts as I watched her succulent titties bouncing. When I finally reached my climax, I whipped my cock out and, pumping it in my fist, shot my load onto Dana's belly. Almost immediately, I collapsed beside her and we were both soon asleep.

Sometime later, with the first rays of sun peeking through the blinds, I awoke to the pleasant sensation of another extraordinary blow job. I blinked the sleep from my eyes and looked down to see Dana happily sucking my cock. When she realized I was awake, she crawled up and straddled me, hanging her fleshy globes right in my face. She took my throbbing cock in hand and guided to her hot, wet pussy. She lowered herself onto it, engulfing it in her snug confines, then started to slowly ride me. I just lay there letting her do all of the work while I sucked on her hard nipples and caressed her soft, smooth tits. Her pussy felt so hot and so wet that I knew it wouldn't take long before I was blowing my load. The question was really how worked up she was because I didn't want to leave her unsatisfied. Fortunately, she picked up her pace very quickly and was soon riding me hard and fast. Based on this and how her pussy was continuing to feel even hotter and more engorged, I suspected that she was well on her way to an orgasm.

I had no idea how long she'd been sucking my cock before I'd awakened but, I had to guess that she must have been pretty horny from the get-go to just start blowing me as I'd been sleeping. As she was obviously getting closer to cumming, I moved my hands down to her curvy waist and held it while pushing up into her each time she came down on me. With her titties unencumbered, I was watching them as they bounced hypnotically right in front of my face. With her pussy continuing to become even hotter and wetter, I could feel my own orgasm building and suspected that, though she would probably cum first, I wouldn't be far behind. When she went from riding me hard and fast to seeming to go into slow motion, it was just a moment later that her entire body was trembling as she gasped.

"Are you almost there?" she asked once she'd apparently finished cumming, "I'm on the pill if you want to cum inside me."

I acknowledged that I was close and she went back to riding me at a pace that allowed me to relish the building pleasure from her hot, slippery pussy for a bit longer. I was still watching her bouncing tits, thinking that it would be a treat to fuck them but not wanting to stop long enough to reposition, even though I was assuming that this would be my only opportunity. Her pussy just felt too good, though, as its snug, slippery grip moved up and down my throbbing tool. As my orgasm grew even closer, my cock was swelling even more within her, making her pussy feel even tighter around it and bringing on my orgasm even faster. Finally, with a moan I exploded into her, filling her hot pussy with my load. She continued to ride me as I was spurting into her, stopping only once I was fully spent and climbing off of my softening cock.

She lay beside me and, as we were recovering, we discussed what had happened, agreeing that, though we both thoroughly enjoyed it, it was a one-time thing and, once I was out the door, it would never be spoken of again. If Jim or Lori asked, I had left the room to sleep alone on the couch and Dana had left to sleep alone in her mom's bed, neither realizing the other had left, too. Though we felt some guilt over Rob, it was just a chance encounter and we figured what nobody else knew wouldn't hurt him.

After that morning, there was no indication that anything had gone on between us - no increased flirting, no flashing and no innuendo. We went on with our lives as if nothing had happened. I basically put the whole event out of my mind and assumed that Dana had done the same. I soon discovered that I was wrong.

Dana regularly stayed with Rob given that his room had more privacy than her room at home. It was not unusual for Dana to stay in Rob's bed for a few hours if Rob had to go to work on a Saturday. It was one of those Saturdays when Dana surprised me.

I was teetering on the brink of waking up when I heard a soft tapping at my bedroom door. Dana came in and said that she'd heard Rob's train pull away and had waited long enough to know for sure that he had made it and wouldn't be back any time soon so could she jump in bed with me? During my split second consideration, I recalled Dana's amazing oral skills, her ample breasts and her hot pussy. There was no way I could deny her. Since I was naked (and sporting a rising woody) I told her she could join me but pajamas weren't allowed in my bed. She quickly unbuttoned her satin nightshirt and dropped it to the floor revealing her milky white globes and close-cropped brown pubes. I turned down the covers and she joined me, immediately grabbing for my cock.

Discovering my excited state, Dana wasted no time in straddling me, draping her huge tits right in my face. She had obviously been anxiously awaiting Rob's departure because her pussy was incredibly hot and incredibly wet. We both moaned as my cock filled her while I grasped her tits and licked and sucked her nipples. She started rocking up and down on my cock, a hand planted on either side of my head, pursuing an orgasm that didn't seem like it would be that far off. Likewise, as she rode me enthusiastically, I could feel my own orgasm building from the moment my cock had been engulfed in her hot pussy. I was perfectly okay with cumming quickly as long as she got off, too, so I was pushing up into her each time she rocked back, giving her the full length of my cock.

It didn't surprise me when she slammed herself down on my cock and just sat there as her entire body trembled. I continued to lick and suck her hard nipples while fondling the soft, smooth flesh of her tits while she came and suddenly found myself inspired. I waited until she had apparently finished cumming and had opened her eyes then asked her to roll onto her back. I got up and straddled her, laying my cock between her succulent tits. Squeezing them together, I started to fuck her cleavage, closing my eyes and moaning at the pleasurable feeling. Opening my eyes again and looking down, I saw that Dana was staring at my cockhead as it appeared repeatedly from her cleavage. I was more focused on her large, pink areolas and hard nipples which I was brushing my thumbs over as I held her tits together.

I savored the feel of the soft, smooth flesh against my tool as my orgasm continued building. I couldn't help picking up the pace the closer it got, though I was trying not to fuck her tits hard. I was sliding the full length of my cock between her succulent tits, my cock swelling even more the closer I got to cumming. Finally, with a groan, I started spurting onto her sternum as her eyes went wide and she stuck her tongue out. Only once I was completely spent did I release her tits and move off of her. I watched her cleaning my cum off her chest with her fingers, feeding it into her mouth. While she lay there cleaning herself up, I took a quick trip to the bathroom to empty my bladder.

Seeing her sprawled out naked on the bed upon my return, apparently finished consuming my cum and appearing quite content, I decided that I wasn't quite done yet. I climbed over her in a sixty-nine and slipped a finger into her snug pussy while attacking her clit with my tongue. She wrapped her lips around my member and I felt it growing again in the warm confines of her mouth. As good as it felt, I wondered whether it would be possible to cum before I was even fully erect. She again marveled me with her oral skills as I devoured her pussy. I felt my orgasm building as her pussy was becoming even wetter and more engorged, leading me to wonder whether she typically came faster after her first orgasm. I knew that I typically required a bit of recovery time but she had me erect again and on the verge of cumming pretty quickly. It wasn't much longer before we came nearly simultaneously, her pussy flooded with additional lubrication as her body shook while I was blasting a load down her throat. She swallowed my load as I continued devouring her pussy until she'd apparently finished cumming. I climbed off and lay next to her.

After a brief rest, we decided to shower together before getting on with our days. We headed down the hall to our small bathroom, not bothering to cover up, though Dana picked up her nightshirt and tossed it into Rob's room. Squeezed into the small shower, we soaped each other up, paying particular attention to each other's intimate parts. I spent a lot of time on her luscious tits and she on my cock and balls. We were soon fully aroused again. We could barely wait until we had toweled off to get into it again. I sat on the toilet and Dana straddled me, engulfing my throbbing cock once again in her hot, snug pussy, but the space proved to be too confining. After a few minutes of combined pleasure and discomfort, I had Dana dismount and led her to the kitchen, around the corner from the bathroom. I sat her on the edge of the table, had her lay back and hooked her knees over my arms.

She guided my cock into her pussy and I pulled her toward me as I fucked her. I watched her tits bounce forward and back then glanced down at my shiny cock sliding in and out of her. She reached down, covering her bush with her hand as she stroked her clit. She'd already shown that she came pretty quickly so I suspected that this would get her there even quicker. I was able to reach forward and caress her boobs as I was fucking her, thinking that I should take advantage of the opportunity since I didn't know if or when I'd get another chance. I'd felt a little guilty after the first time we'd been together and had fully intended to put it behind us but this time I was relishing her body, both the way it felt and the way it looked. I admit that I was a little envious that Rob had somebody who was quite obviously very sexual and didn't seem to have any trouble cumming. Who'd have known at that time that I'd end up involved with a significant number of women who were quite similar to Dana in that respect?