So Very Wrong

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.

I was already home from college for the summer, but Annie was still a couple of weeks away from graduating from high school; an event that might be complicated a bit by the injury to her ankle. When I called her house that day, it may have been the first time I'd spoken to her since shortly after I'd returned to school following spring break. She didn't seem to hold it against me, though; in fact, she seemed pretty excited to hear from me, which certainly made me happy given that we had an entire summer stretching out ahead of us. We'd come close to hooking up back in high school, but the logistics had never quite worked out. When I was home over Christmas break, however, we'd run into each other at a party and had spent some time together. Once I was back at school, we'd kept in touch pretty well at first and I'd promised to take her out for her eighteenth birthday, which was in February, when I was home on spring break a month later. We'd seen each other a bit during my break, but communication fell off once I was back at school and we both got busy. That was why I was glad that she still seemed excited to hear from me when I called.

I'd heard about a party that night and had wondered if she'd be interested in going with me, which is when she let me know that she was laid up with a severely sprained ankle. It had only been a couple of days since the injury, so she wasn't going to be able to get around on it quite yet. I figured I could hit the party later if I still felt like it and asked if it was okay for me to stop by since seeing her was really more of a priority for me. She was good with it, so I told her that I'd see her later. I didn't expect an opportunity for things to go too far at her parents' house but I did want to see her and get a better sense of what the summer might have in store for the two of us.

I was so one-tracked on seeing Annie that I had completely spaced on seeing her mom. It was obvious where Annie and her two older sisters got their looks because their mom was a total MILF. She opened the door wearing what looked like a tennis outfit, a short sleeved dress with a very short skirt. The thing was that I didn't have to fight to keep my eyes from drifting down to her legs because her pretty face kept my attention. I was surprised that she seemed almost as excited to see me as Annie had sounded to hear from me, but I guessed that she was just happy that there was still something between Annie and me. When she turned to escort me to see Annie, I did take a look at her legs and how nice her ass looked above the hem of the short skirt.

In the family room where Annie and I had made out a couple of times a few months prior, Annie was sitting with her ankle up on a pillow on the coffee table, watching TV with her best friend Mary Ellen. Good friend that she was, Mary Ellen stuck around just long enough to say hello, then excused herself so that Annie and I could catch up.

"Feeling any better?" I asked.

"I am now," she replied with a smile, then leaned toward me. We kissed, then made out a little bit.

"Anything more I can do?" I asked when we came up for air.

"I don't think a massage would hurt," she said, using our code word for when we'd gone to third base the last time we'd been together. I was pleasantly surprised and definitely wouldn't deny her request but, rather than continuing to make out, we tried to make it less obvious as I slipped my hand into her shorts. I positioned myself so that somebody would have to make it all the way into the room to realize what was happening as her good leg lay across my lap and my fingers crossed her trim bush to find her dripping pussy. She stifled a moan as I caressed her clit before slipping a finger into her tight, wet pussy. She gyrated her hips as I pumped my finger in and out a few times before returning my fingertip to her clit.

She gasped this time and I noted that her eyes were closed but she had a look on her face that told me she was experiencing some intense pleasure. Each time I dipped my finger back into her pussy, it felt more and more engorged as she appeared to be getting closer and closer to cumming. She was getting there pretty quickly, so I wasn't too concerned about the chance of being interrupted. Naturally, we were interrupted.

"Annie, your mom wants to know..." Mary Ellen started as she entered the room, "Oh my God, I'm sorry."

"Mary Ellen, wait," Annie said while grabbing my hand so I didn't try to slip it out of her panties, "he's got a free hand and I guarantee you don't want to miss out on this."

As Mary Ellen stood and thought for a moment, I started to stroke Annie's clit again and she let out a soft moan, which may have been for Mary Ellen's benefit. Mary Ellen sat on my other side and I repositioned again so that I could slip a hand into her shorts, once she'd unbuttoned them. I caressed her pussy through her panties first as she spread her legs wide and let out a sigh. As Annie returned to the point she'd been at when Mary Ellen had walked in, I slipped my hand into Mary Ellen's panties and my fingertips traced over her trim bush. She sucked in her breath as I lightly caressed her clit while, on the other side of me, Annie was rocking her hips faster and faster. I slipped a finger into Mary Ellen, finding her as tight as Annie and nearly as wet. I pumped my finger in and out a few times before focusing on lightly stroking her clit.

As Mary Ellen's soft breathing was picking up on one side, Annie was struggling not to moan out loud on the other. She tensed up more and more until, after going rigid for a moment, she started to tremble while moaning softly. I continued to caress her clit, just as I continued to caress Mary Ellen's, but once she'd finished riding out her orgasm, she had me remove my hand from her shorts and reached over to massage the front of mine. My cock was rock hard, so I appreciated the attention, but it would end up a lot more difficult to act casual if someone was to walk in at this point. Annie apparently didn't care, however, because she opened my shorts and extracted my tool, pumping it in her fist as she tried to reposition herself slightly while keeping her ankle elevated.

I don't think Mary Ellen was aware of it when Annie engulfed my throbbing tool in her mouth and started to slide her lips up and down it because she had her eyes shut and her hips were starting to move more. As with Annie, when I dipped my finger into her tight, slippery pussy, I was finding it more and more engorged, so I knew she was well on her way. I just tried to stay focused on providing pleasure to her and not get completely distracted by the pleasure that Annie was providing to me. Mary Ellen gradually started tensing up, just as Annie had right before she'd cum and, as Annie continued to suck me off, Mary Ellen went momentarily rigid before starting to shake. A soft cry escaped her lips as she came so Annie removed my cock from her mouth and looked up at Mary Ellen while continuing to pump it. I slipped my hand from Mary Ellen's shorts once I was certain that she'd finished cumming and tasted my finger tip as I'd done with the hand I'd used on Annie. Their flavors were similar but not exactly the same and I wondered whether I'd have an opportunity to eat Mary Ellen's pussy as I now expected that I'd be eating Annie's sometime soon.

"You want to help me out with this?" Annie asked Mary Ellen, who then opened her eyes and looked down to see Annie pumping my tool in her fist. Mary Ellen moved off of the couch and Annie offered her my cock. I had nothing to do but enjoy as I felt Mary Ellen engulf my cock in her mouth. I let one hand rest on her head, not pushing but caressing her long, black hair, as the other hand reached around to cup Annie's small, perky tit. They alternated back and forth, each of their hot mouths taking several trips up and down my tool before the other took over. It didn't take long at all before my cock began to swell even more though I tried my best to just relax and enjoy the pleasure I was feeling for as long as I could. Soon, though, it was just a question of who would receive my bounty. I didn't know if I'd ever have another opportunity to cum in Mary Ellen's mouth, so I really wanted it to be her; I figured I'd have all summer to cum in Annie's mouth.

As it turned out, I started to spew into Mary Ellen's mouth but she was generous enough to share my load with her best friend. That was just fine with me and I continued to relish their attention until I was completely spent and my cock was starting to soften. The two of them resumed sitting beside me and adjusted their shorts while I tucked myself away. We didn't discuss what had transpired; just watched TV for a little while. I figured they would talk about it between themselves and Annie and I would probably talk about it after that, but my head was still kind of reeling that it had happened at all so I had no desire to talk about it yet. At one point, Annie's mom brought us some cookies she'd baked and some milk and I realized that Mary Ellen had been sent to ask us something about that when she'd walked in on us.

Before it got too late, I told Annie that I should go and that I'd call her the following day to check on her. She still seemed happy that I'd stopped by but Mary Ellen seemed to be feeling a bit awkward, so I figured it'd be good to leave them alone. I stopped in the kitchen to thank Annie's mom for the cookies and we talked for a few minutes before she walked me to the door, thanking me for coming by to see Annie on a Saturday night when she knew there were probably all sorts of parties that a college kid like me had been invited to. I gave her a hug before I walked out and, despite having cum in her daughter's mouth not that long prior, I still felt a stirring in by shorts when her body pressed against mine.

When she didn't make a move to step away immediately, I just hung on and enjoyed the feeling of a forty-something woman in my arms. When she nuzzled my neck, I decided to go for broke since my luck had been incredible already that night, and dropped my hands down to her ass. She let out a soft whimper as I caressed her ass, pulling her against my growing cock then she kissed my neck. I didn't want to let go, but I also didn't want Mary Ellen or, worse, Annie to see us, so I was actually relieved when she whispered that she should probably walk me to my car. As we headed out the front door, she reached over and flipped the switch that turned off the post light that was down by the driveway. It wasn't pitch dark when we reached my car, but dark enough that no one was likely to notice us standing there as we started to make out. I seriously was concerned that I'd wake up alone in bed at any moment because I could not fathom this not being a dream but I certainly planned to roll with it. In the meantime, as we made out, my hands were back down on her ass and my cock was growing against her abdomen.

I started to work her skirt up so that I could get my hands on her ass with less material in between and, no sooner did I have my hands on her panties than I wanted to have them on her bare ass. Her ass certainly felt as spectacular as it had looked wrapped in the dress but I knew that, despite the dark, I was definitely planning to take a closer look at it. While I started sliding her panties down, I was also dropping down to squat in front of her. I helped her step out of her panties then tossed them onto the hood of my car before raising the front of her skirt. There was enough light out there that I could see the dark brown of her bush and, as I leaned in to kiss the area around it, she took over holding up her skirt while leaning back against my car and spreading her legs.

I ran my tongue up her slit, finding it overflowing with pungent juices and causing her to exhale loudly. She held the back of my head as I lapped at her pussy and gyrated her hips in rhythm with my licking. I wanted to go back to squeezing and caressing her sweet ass while I ate her pussy but, since she was leaning against the car, I couldn't and had to find something else to do with my hands. I was just caressing her smooth thighs until I focused my licking on her clit, when I slipped a finger up into her hot, wet pussy. It was no surprise that she wasn't as tight as Annie and Mary Ellen had been but she was so slippery that I was able slip a second finger in along with the first, causing her to gasp. I pumped them in and out while licking and sucking her clit and she appeared to be having a tough time keeping her moaning under control.

Not unlike Annie and Mary Ellen, the longer I ate and fingered her pussy, the more engorged it became as she got closer and closer to cumming. She was humping my face while holding the back of my head as I relished the fact that I was not only devouring the pussy of an older woman and the mother of a girl I was planning on getting similarly intimate with, but that I had her on the verge of what appeared to be a pretty intense orgasm. My cock was throbbing again and, whether it went into her mouth or her hot, wet pussy, I had no doubt that Annie's mom would take care of me once I'd finished taking care of her. When she suddenly started to shake and twitch, I knew that I'd accomplished my goal.

I continued to eat and finger her as she rode out a long, intense orgasm, stopping only once she'd let out a long sigh. I slipped my fingers out of her and into my mouth, sucking her juices off as I stood up again. I had to move my hand as she pulled me toward her again so that we could go back to making out, though this time she went right to work on my shorts and soon had my throbbing cock in her fist. She hopped up onto the hood of my car and spread her legs, guiding my cock to her pussy, which I easily slid into as we both moaned softly while continuing to make out. Despite not being as tight as the girls my age who I was accustomed to, her pussy felt incredible and, as I started to slowly fuck her, I could feel her working muscles in it that I had never felt before.

I still had no access to her ass so I leaned on the hood at first, then brought my hands up, first to her waist, then to her tits. She was wearing a bra under the dress but I caressed her tits through both it and the dress and could feel her hard nipples. She had her arms around my neck and her legs wrapped around mine but couldn't really do much more than work her pussy in that position. Though I was without a doubt enjoying fucking her on the hood of my car, I thought there might be a less restrictive position that would allow both of us a bit more control.

"How about if you turn around and lean on my hood?" I asked softly in her ear.

"Okay," she agreed, so I slipped out of her and backed up as she hopped down and turned around. I flipped up her skirt and pushed it up around her waist once she'd leaned forward and rested her head on her arms on the hood where her ass had just been. I took the opportunity to massage and caress her sweet ass before guiding my cock back into her. Taking her by the hips, I started to fuck her again and, once I had a rhythm going, my hands went right back down to her ass. She was pushing back against each of my incoming thrusts, appearing to appreciate having some control over what was going on. As we started fucking harder, my hands were getting in the way, so I moved them up to her waist, then slipped them up under her dress to cup her tits. As I was unfastening her bra to get my hands on her bare tits, she slipped a hand down between her legs, I assumed to massage her clit.

The longer we fucked, the better her pussy was feeling so I was starting to feel the stirring of my approaching orgasm. I knew we were pushing our luck just with the amount of time we'd spent together in the driveway, but I still wanted this experience to continue so I wasn't necessarily looking forward to cumming. I relished the feel of her swinging titties in my hands and her pussy sliding up and down my tool, not knowing if I'd ever have the opportunity again. As she was pushing back against me harder and harder, I wasn't really focused on whether she was going to cum again, so when she started to tremble, I was pleasantly surprised. I continued to fuck her and fondle her tits as she came, feeling my orgasm building even more quickly due to the increased lubrication she was producing. Once she'd finished cumming, before I was quite there, she straightened up and moved so that my cock slipped out of her.

She turned and kissed me again while rotating me so that I could lean against my car then hunkered down in front of me and took my cock in her hand. She pumped it briefly before wrapping her lips around it and sliding them down while holding the base. I ran my fingers through her hair as she expertly sucked my cock while pumping the base with one hand and fondling my balls with the other. I had been extremely close to cumming when she'd cum so it didn't take much of her talented cocksucking to have me back on the verge again. Despite the risk we'd already taken, she still did what she could to prolong the pleasure she was providing, though I'm not sure whether it was for my benefit or for hers. As excited as I was about being with an older woman, I couldn't help but wonder if she was similarly excited just because I was much younger than she was.

My eyes had become very well adjusted to the dim light by this point, so I was able to watch her as my cock disappeared repeatedly in her mouth and it was certain to be a vision that I'd never forget. Even as my cock swelled more and I was consciously holding back moans, I never closed my eyes and just watched her. Because I was trying to stay quiet, I think my orgasm surprised her a little bit, but she kept right on going even as I was spurting down her throat. She swallowed my load and nursed every drop from my cock, finally letting it fall from her mouth once I was spent.

She immediately started helping me get my shorts back up, so I tucked myself away as she tried to refasten her bra. I raised her dress up high enough to do it for her and caressed her bare ass some more while lowering her dress back down.

"May I hang onto these for a while?" I asked as I reached over and grabbed her panties.

"Only until we have an opportunity for me to give you another pair," she replied.

We made out again then talked briefly about when we might be able to see each other again and how important it would be that no one even suspect anything was going on between us. I finally took off and headed over to see if the party was still going on so I could show off her panties, though I did keep the identity of the owner a secret. We managed to see each other occasionally that summer, though I spent most of my time fucking Annie, with Mary Ellen joining us for a threesome on several occasions. It was probably very wrong what I was doing that summer, but damn did it feel so right.