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 fiancΓ©, 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 fiancΓ©, 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.