The Grieving Process Ch. 03

Note: If you haven't already, read The Grieving Process Ch 01 & 02, which are prequels to this story.

As soon as I knew that I'd be back in town again, in addition to contacting Theresa, I also let Emily know that we'd finally be back together physically once again. After all of the time we'd spent naked together during my previous visit, we'd since been limited to sharing photos and videos and the occasional video chat. I knew that, if the time I was expecting to spend with Theresa didn't actually end up with us naked, I'd at the very least be getting naked with Emily. Since I wouldn't have a hotel room all to myself this time, though, coordination was likely going to be more complicated but we were both committed to doing whatever we could to make it work. She actually said that she'd have no problem coming to my brother's house even if he was home if that was what it would take for the two of us to be naked together again. It ended up working out that the first time she was available to come over once I was in town was during one of the times that my brother was gone but, since he was aware by that time of what had happened with Theresa, we hadn't made any special effort to make sure of that.

Since we'd been able to spend a considerable amount of time together in my hotel room the last time I'd been in town, there was very little that we'd left undone. Being limited to photos and videos since that time, though, had us eager to be together physically once again. She arrived at his house dressed conservatively enough on the outside but I suspected that, like our first afternoon together, I'd find some sexy lingerie underneath. I let her in and we briefly but passionately kissed before I locked the door and led her to my bedroom. I also locked that door behind us then we made out as we began to undress each other. I was wearing just jeans and a t-shirt, the same as the first time we'd undressed together, and she was wearing a dress again, but this time without all of the buttons. I'd suggested that our enthusiasm to get naked might result in a few popped buttons that could be difficult to explain once she returned home. She liked to wear dresses so she had plenty to choose from and promised she'd wear one that would be easy to get out of without raising any suspicions when she left home wearing it.

She was pulling my shirt up over my head as I was caressing her ass so, once we'd parted so that she could remove it completely, I started to pull her dress up. She raised her arms and, as her lingerie came into view, my jaw dropped and my cock stiffened even more. This was definitely something I hadn't seen before and it looked outstanding on her. Her big boobs were practically spilling out of a low-cut, lacy black bra and the matching panties were my favorite style, as she well knew, bikini. Still holding her dress, I backed up with my mouth hanging open and my eyes wide, just taking her in.

"I definitely have not seen you wearing this before," I finally managed to say.

"No, I bought this new just for this occasion," she replied.

"I want to see it on you and take it off you at the same time," I said, "but I'm going to take it off so I'm going to need photos."

"I've already taken a bunch for you," she replied, "but I didn't want to ruin the surprise. I'll send them later so let's get naked now."

I dropped her dress then moved closer and reached around her to unfasten her bra while bringing my lips to hers again. As I worked to unfasten all of the hooks required to hold up her big beauties, we made out again until I was ready to slip it off of her. I stepped back while sliding it off her shoulders and down her arms, exposing the rest of the fair and flawless flesh as well as her large, pink areolas. I dropped her bra and reached out to caress her succulent tits, running my hands over the soft, smooth flesh and her hard nipples. While I was doing that, she got my jeans open and pushed them down far enough for my rigid cock to spring out. She gently stroked it but that wasn't what she wanted.

"I need this inside me," she whispered so I reluctantly abandoned her boobs and pushed my jeans down farther so that gravity carried them to my ankles. After stepping out of them and kicking them aside, I hunkered down in front of her and slid her bikini panties down, revealing her trim, light brown bush. As she was stepping out of her panties, I planted a kiss on each of her hips and her lower abdomen before standing again. We climbed onto the bed and I lay on my back while she straddled me. As she was guiding my cock toward her pussy, I resumed fondling her big boobs. We both moaned as she lowered herself onto my cock, her hot, wet pussy engulfing my full length. She just sat on it for a moment, feeling it inside her, as I continued to caress and fondle her tits. It was awesome to be with her again after seeing her only in two dimensions for so long. Feeling the soft, smooth flesh of her tits while my cock was engulfed by her hot wet pussy, it felt like it had all been worth the wait. When she started to slowly move up and down on my cock, I was certain of it.

She started out slowly but gradually picked up the pace until she was riding me hard and fast. Fortunately, the bed was sturdy and well-built so it wasn't making any telltale noises, not that there was anyone else around to hear it. Once her tits started bouncing, I moved my hands around to caress her ass while watching them. They were definitely more spectacular in person than they had been in all of the photos and videos. Her moaning was becoming louder and longer as she continued moving up and down on my cock and I pushed up into her each time she dropped down. I could feel the stirring of my orgasm because her pussy felt so hot and so wet but it was sounding as though she'd be getting there before I did. It didn't surprise me that she was building up to an orgasm so quickly. Not only had there been a great deal of anticipation leading up to this but I had learned during all of the time I'd previously spent with her that she had no issues with being able to cum, typically easily and intensely.

I had no problem if she came quickly as long as it was a highly pleasurable orgasm. I knew that, if she didn't continue riding my cock after she'd cum, she'd switch to something equally enjoyable. I also wasn't concerned about cumming too quickly myself because I figured that, if I did, we'd just have more time to recover and go at it again before she had to leave. In the meantime, I was focused on the pleasure I was feeling as her pussy continued to become even hotter and wetter while I watched her titties bouncing. Being with her again was everything I remembered from my previous visit and definitely lived up to all of the anticipation I'd been feeling since I'd learned that I was going to be back in town. I suspected that she was feeling the same way.

When she finally just dropped down onto my cock and remained there, she went silent for just a brief moment then let out a cry as her body started shaking. Since her boobs were no longer bouncing, I brought my hands back around to fondle them again as she was riding out what appeared to be one of her typically long and intensely pleasurable orgasms. Instead of starting to ride me again once she'd finished cumming, she got up off of my cock and swung herself around so that she could straddle my head. I gazed up at her trim, light brown bush as she gently gripped my cock and pumped it before wrapping her lips around it. I moaned as her warm, wet mouth engulfed my tool and she slid it up and down while continuing to pump the base. I savored her oral skills for a moment before raising my head and running my tongue along her slit. Her pussy was flooded with juices, which I initially focused on lapping up and, based on her moaning around my cock, must have been feeling pretty good to her.

I had devoured Emily's pussy multiple times during my previous visit and, although I couldn't say that I necessarily recognized her flavor or could have distinguished it from Theresa's, I was stoked to be tasting it again. I enjoyed eating pussy anyway but, to have another opportunity to eat hers, that was a really special bonus. Consequently, I was truly savoring it, from lapping up her juices to slipping a couple of fingers into her to licking and sucking her clit, which had her moaning even more around my stiff cock. Of course I was also savoring her oral skills as she was enthusiastically sucking my cock. She left nothing to be desired when it came to cocksucking which she'd been so grateful to hear during our previous time together. She'd explained to me how she'd married her high school sweetheart, which I knew, but confessed that she was nervous about sucking his cock and refused to do it for a long time. It was her girlfriends who convinced her to give it a try and she'd enjoyed it nearly as much as he had. From that point on, she really enjoyed sucking cock but had never done it for anyone else. Knowing that I'd only be in town temporarily, she'd decided that, if she was going to see what sucking another cock was like, mine would be ideal. Plus, my first reaction to seeing her was to describe her as "yummy" so she felt like it was a good bet that I'd be down for it.

I still found her yummy, not just the taste of her pussy but her curvy MILF body in general, which I'd thoroughly explored during my last visit and planned to do again. First, though, I wanted to just focus on eating her pussy and making her cum again while enjoying the build-up of my own orgasm. My fingers were sloshing in and out of her pussy because she was so wet and, although I knew she was getting close to cumming as things were, there was something else that I knew she would absolutely love. While still licking and sucking her clit, I slipped my fingers out of her pussy then slathered her own pussy juices around her asshole before slipping one of my fingers into it. She immediately let out a cry of pleasure and her body started shaking. I eased my finger in and out as she was cumming though it was hard to tell if that made her cum any longer or any harder than she would have otherwise. There was no question that she experienced an extremely high level of pleasure, however.

When her orgasm finally tapered off, she resumed sucking my cock even more enthusiastically. It wasn't like she was trying to make me cum more quickly but was putting her efforts into providing the highest level of pleasure rather than in drawing out the pleasure. I slipped my finger out of her ass and let my head drop back, gazing up at her pussy while I felt my orgasm building and knowing that it wouldn't be much longer before I was spewing into her mouth. I reached down and found her dangling tits and, as I hefted their weight and felt the soft, smooth flesh, it felt as though my cock became even harder. Her efforts were not affected, however, and she just continued to take as much of it into her mouth as she could manage while pumping the rest in her fist.

When I finally exploded into her mouth, the level of pleasure was incredibly intense and my orgasm seemed to just go on and on. She continued to suck me off while pumping the base of my cock as she swallowed my load. Only once I was completely spent did she let my cock fall from her mouth and raise her head. She moved off beside me so I sat up and moved around then we lay side-by-side as we recovered.

"I'm so happy to be with you again," she finally said, "I wasn't sure we'd ever get another opportunity."

"I wouldn't have said that the circumstances are ideal," I replied, "but I am glad you are available and interested in helping me through this."

"Of course," she said, "I was feeling a little selfish because I just wanted to be with you but, if you feel like I'm helping you by being here, that helps me to rationalize it."

"There's no doubt that you being here is beneficial," I assured her, "It could feel like a very dark time otherwise."

I couldn't help but reach over to fondle her succulent tits as we were chatting. Although the photos she'd shared showed how spectacular they were, two dimensions really didn't do them the justice they deserved. I soon lowered my head to lick and suck her nipples while I continued to fondle them and she began to moan softly. As I also ran my hands over her stomach, waist and hips, feeling the soft, smooth flesh that I'd been missing since I'd last had my hands on her, my cock was reviving admirably. I ended up getting up on my knees so that I could look over her yummy body while it continued to stiffen. She seemed to be pretty relaxed and enjoying the feel of my hands on her when suddenly her eyes opened and she sat up.

"I almost forgot," she said, moving to get off of the bed, "I have a surprise."

She grabbed her purse as I gawked at her naked body then extracted a bag containing what turned out to be a bottle of lube and a pack of pre-moistened wipes. My cock immediately became rigid. During my last visit, we'd been showering together when I'd slipped a soapy finger into her ass while eating her pussy. She'd cum so hard and so intensely that she asked me to soap up my cock and slip that into her ass. As soon as I did, she had an orgasm so intensely pleasurable that her knees had nearly given out. She'd managed to hang on through a couple more orgasms before I had to quit to prevent her brain from melting inside her skull. We tried this a few more times before I left town and I actually managed to cum in her ass a couple of those times. She'd never had, or been interested in, anal sex nor had her husband ever pushed for it, but she'd apparently missed it in my absence. The lube was obviously to make penetrating her easier and the wipes were to clean up as necessary since we weren't in the shower.

While I got the wipes open, she got the lube open and applied it to my stiff cock. Then, as she was wiping her hands off, I took the lube. She got onto the bed on her knees with her ass up in the air and her face on the comforter so I drizzled the lube on her asshole and spread it around, both inside and out. After wiping the excess off of my hands, I got behind her on my knees and lined my cockhead up with her asshole. As soon as I eased it inside, she started shaking while crying out into the comforter. I began to slowly slide my cock in and out of her ass while she was cumming, which may have actually prolonged the pleasure she experienced. I was glad that it was already paying back her investment and figured that it was probably also living up to any hopes or expectations that she'd had.

I continued to slide my cock slowly in and out, relishing the pleasure that her snug, lubed backdoor was providing. Since I'd just cum not that long ago, I expected that I'd be good to fuck her for quite a bit despite how snug and slippery her asshole was. She, on the other hand, experienced what appeared to be another intensely pleasurable orgasm not too long after the first. Since she was on her knees, I wasn't worried about them giving out on her but there was still the risk of her brain melting inside her skull. I maintained a slow pace just to make sure that she continued to feel pleasure rather than discomfort. I didn't need to fuck her ass hard and fast to enjoy the snug, slippery grip but that meant her ass wasn't jiggling each time my hips met it so I leaned forward slightly and slipped my hands up to cup her dangling tits. My cock may very well have become stiffer or thicker or both because almost immediately she came again. Once that orgasm had run its course, she had me stop and slip out of her.

"I never would have expected to enjoy that as much as I do," she explained, "but it actually causes pleasure overload and I'm afraid I may lose control of my body."

I was fine with switching to something else and was just happy for the opportunity to fuck her ass again, however briefly. She grabbed a wipe and reached back to clean the lube from between her cheeks but stopped me when I was going to clean it off my cock. She repositioned herself lying on her back and drizzled some lube between her tits. I straddled her and lay my lubed cock between her lubed tits then squeezed them together and began to fuck them. Fucking her tits had always felt incredible but fucking them with all the lube was unbelievable. Any expectation of being able to last longer because I'd cum once already went right out the window and I was completely fine with it. I was looking down, admiring her luscious titties as I was both fucking them and caressing them while I held them together. She was watching my cock as it peeked repeatedly from her cleavage. I'd made no secret of the fact that I loved fucking her big, beautiful titties during my last visit so she seemed less amused by this act than she had been.

As with when I'd been fucking her ass, I maintained a slow pace because fucking her tits harder and faster wouldn't likely feel very good for her, even though it quite possibly could for me. I was actually enjoying the slow build-up, especially since fucking her ass had been short lived. As hard as she'd cum while I was fucking her ass, I also didn't feel bad that she probably wasn't getting anything out of me fucking her tits. Despite the slow pace, though, my orgasm did continue to build steadily and, when my cock started to become even thicker and harder, I wondered if she could feel it through her tits. When she opened her mouth, as though expecting me start spewing toward it, I suspected she could feel that something was changing as I was getting closer to cumming. Of course, as quiet as it was in the room, she probably could have detected a change in my breathing rate or the volume of my moaning. Whatever the case, when I did finally start to spew, she was ready and my first couple of spurts hit her right in the mouth. The next few were weaker and left a small pool on her sternum but I was still sliding my cock between her tits until I could no longer successfully do so.

I moved off beside her, remaining on my knees, and watched as she was running her fingers through the cum on her chest then licking it off. Once she'd consumed as much of it as she could, she had me pass her a couple of wipes and worked on getting the lube cleaned out of her cleavage while I took one and wiped down my cock. We lay together for a little longer after I tossed the wipes into the trash but she soon declared that she needed to get going.

"Okay," I said as we were both getting up, "but you have to assure me that you'll be coming back, otherwise the door stays locked and you'll be stuck here with me."

"I promise I will be back," she said, "but don't believe for a second that the idea of staying here isn't appealing to me."

She suggested that it would be safer if I was to keep the lube and wipes, which I ended up using with Theresa, too, since I had them handy. Even though she'd told me that she'd be sending photos of herself in her new lingerie, I still took a bunch as she gathered it up and pulled it back on. Once she was covered, I pulled my own clothes back on then we gave each other the once over before I unlocked and opened the door. We could hear more than just my brother's voice as we headed down the hall and it turned out that all of his adult kids were visiting. The look on his face when he saw Emily with me was priceless and, as she hugged him while expressing her condolences, his expression could best be described as incredulous. I'm sure my expression was once again something like the cat who ate the canary. After a few minutes, I walked her out to her car where we hugged but otherwise kept things innocent looking to the casual observer. Heading back up the walk, my oldest nephew was standing on the front porch.

"She was walking like she'd recently been fucked in her ass," he casually commented.