Lucy Strays Ch. 03

I often times found myself checking her out. Objectively, she was slightly prettier than my wife, but I would never admit that in public. But now, here she was completely exposed for me to see...a fantasy come true. I grabbed my cock, trying to time my strokes with hers.

As if my fantasy couldn't get any better, she turned to a doggy style position, and continued to play with herself. Her breasts looked amazing hanging down, jiggling with her movements. Lucy has nice tits, but these I call swingers, and they were mesmerizing. I briefly looked down to see where I could safely finish without leaving an obvious trace. However, when I looked back up, Claire was walking towards me. Shit. Shit. Shit.

"Chris, what the fuck are you doing out there," she scolded me as she pulled her shirt and skirt down.

"I got off work early and figured I would take care of your water heater early," I said, a little defensively.

"Do you always spy on women from their backyards," she challenged.

"Uh..ummm..uhhh, no. I was planning on scaring you when I umm, when I umm saw you on the couch," I stuttered out.

"So, you decided instead to just watch me and jack off out here in my yard where my neighbors can see you," she shot back accusingly.

"Claire, I'm sorry. It's just that you looked so amazing that it was pure fantasy come to life. Please don't tell Lucy. I'll do anything you want," I tried to reason.

"You fantasize about me?" she smiled with an arched eyebrow.

Her line of questioning was a bit surprising. I thought she was going to chop my balls off and then call Lucy, but this was a much better line of questioning, so I pressed forward with the truth and to see what happened.

"All the time Claire. You have an amazing body, and you're a definite MILF" I answered, trying to butter her up.

"Yeah right. I've had two kids and they've ruined my body," was her self-deprecating response.

"Are you kidding me? Claire, you are amazing. At least amazing enough for me to secretly jerk off to in your backyard," I added with a smile.

She looked like she was mulling over what to do when, to my surprise, she told me to come inside.

"You said that you would do anything, right?" she asked me very seriously.

"Ask way. I can fix your car, paint your fence, babysit...you name it. As long as Lucy doesn't find out."

"Well...there is one thing you can help with," she started...." Remember when you saw David's large package the other night?"

"Yeah, but that's kind of weird thing to ask."

"Oh, shoot, how do I say this? Let's just say that David is a bit too large for certain activities that I would like to try...," she began. "I'm sure you noticed, but I've recently become quite obsessed with ass play. Problem is there is no way in hell I'm letting David put his monster hog in my ass. I couldn't help but notice that you were...how do I say...more fit for the job" she finished.

"Whoa, whoa. Are you asking me to take your anal cherry?" I replied flabbergasted at the turn of events.

"I understand if you say no, and I still won't tell Lucy," she seemed to try and backtrack.

"No, no, no. I have wanted to do this a million times, but it just seems wrong. I don't know if I can cheat on Lucy" I said torn between my dick and my brain.

"It's not really cheating is it? I mean doesn't it count as helping a friend lose her virginity?" she asked reasonably.

She kind of had a point. At least that was what my stupid lizard brain rationalized. This was the dumbest argument ever, but I wanted to believe it. I mean could I really turn down the chance to pop Claire's anal cherry? This was a once in a lifetime moment. It wasn't like we were going to carry on a long, emotional affair. A one-time sex act wasn't really cheating I convinced myself. I mean, I had fantasized about this sexy ass MILF about a hundred times, and to make it even better it was her idea, plus, she wasn't going to tell Lucy, and David was out of town so our chances of getting caught appeared slim. I grabbed her hand and led her over to the couch.

Claire had a big smile on her face, apparently very pleased with my choice. As she got to the couch, she removed the butt plug and set it on the end table. During all the talk I had lost my erection, so Claire took it upon herself to bring me back up with her mouth. Wow, her mouth was wet and soft, giving me the smoothest BJ ever, using her tongue to swirl around my head as her mouth moved up and down my shaft.

"This is nice. I can actually get all of you into my mouth, and it doesn't feel like my jaw is going to break," she mouthed between strokes.

Not sure how to take that one honestly. I mean how big was David anyway?? I never had any complaints about my size, but oh well, she seems to be enjoying it, so I pushed that thought to the back of my mind. Once I was nice and hard, which did not take long, Claire turned around presented her ass to me like a dog in heat.

"There should be enough lube up there already from the toy, my juices, and my spit," she said to me over her shoulder.

I was so damn excited I thought my dick would explode. Lucy never lets me play with her ass. She always says it is dirty or not something normal people do. I on the other hand had fucked my high school girlfriend backdoor and enjoyed myself, but that was once, and she didn't really like it. But now I had Claire Parker's magnificent ass pointed at my pole, begging to be fucked. I started by rubbing my dick up and down her pussy first to get lubed up, briefly thinking about sticking it in accidentally, but Clair read my mind and quickly reminded me, only her ass. I didn't need telling twice. I put the head of my cock against her puckered ass and began to slowly push it in.

"Owww. Owww...go slow" Claire whimpered sexily.

I was slightly bigger than her plug I guess, but I thought she would be able to take me no problem after having that in her for so long. Either way I didn't want to hurt her, so I took my time inching it in very cautiously. I had about half my dick in her when I started to pull it back out.

"Ohhhh yeahhhhhh" she deeply moaned into the pillow.

I took this as a sign that she was getting accustomed to my size and on the next thrust I pushed it all the way, so my balls were resting against her wet pussy. She seemed to really like that as her moans and groans were coming at a furious pace.

"Faster now. Really pound my ass," she commanded.

Hell, yeah I thought. I gave her everything I had. When I felt a vibration in my balls, I realized that she had brought her vibrator back out. She was mashing it against her clit as I slammed into her over and over. I used my hands to spread her cheeks apart and watch my shaft penetrate her tight pink asshole. It was so tight there was no way I was going to last long; in fact, it seemed tighter than Lucy the first time we had real sex.

"Oh god, oh god. I'm not going to last much longer. Where do you want me to cum," I managed to blurt out.

"Cum inside me!" she begged.

That did it. I felt my balls tensing up, ready to explode. After using condoms for the last few months with Lucy, it was exciting to go bareback again. I looked in the reflection of the TV to see Claire's huge tits swinging with my thrusts. And that did it too. I grabbed her hips and shoved myself all the way to the hilt, blasting my sperm into her ass.

"Ugghhhhh. Yesss. Yesss. Fuck that's good," I groaned out.

"I'm coming, I'm coming, don't stop, fuck my assssssss." she cried out with me.

Our orgasms seemed to happen simultaneously, which I considered an extra flower in my cap for a job well done. I slowly pulled my softening cock from her backside and watched some of my cum run down her pussy lips. God that was sexy. We lay there collecting ourselves for a moment before she chimed in,

"That was better than I imagined. Thank you, Chris."

"My pleasure. You were amazing. I will think of that for the rest of my life," I said smiling.

Once we finished cleaning up, I did manage to fix her water heater. Then I gave her a peck on the cheek, told her that I would see her around, and made my way home. Lucy wasn't home yet, so I jumped in the shower to make sure there wasn't any potential evidence leftover. Afterwards I headed downstairs to make dinner with a definite extra bounce in my step.

Lucy

Clearly, my libido was firing on all cylinders these days as Chris and I were having more and different sex than usual. He was excited because I was initiating for once, and I was excited because it helped with the guilt. It was easy to rationalize my behavior when Chris was reaping the benefits. Yet, something was still missing from my sex with Chris though. Sure, it was full of love and compassion and all that jazz, but I craved the naughty stuff. David had introduced me to a world of taboo sex and like a drug addict that needs more and more to get high, I was addicted. It certainly didn't help that David was out of town for two weeks. My pussy craved the fullness and excitement that he provided.

Another byproduct of the new me was that I was starting to dress sexier. Not totally slutty of course, I did work in a school, but subtle things that made me feel sexy. I bought some lace topped thigh-highs and a few pairs of sheer panties. I loved the way I could see the top of the stockings if I bent down wearing a shorter skirt, and I liked the contrast of my dark bush against the light colors of the panties. Again, most of this was for me. My intention was not to troll for guys. That was easy enough in sweatpants.

It had been about 12 days since I had had David inside me, not that I was counting, and the "itch" was starting to come back strong. I decided that a good way to placate myself was to wear my new sexy outfit to school. I picked out a knee length black skirt, long sleeved white blouse with a tasteful little window to my chest for some partial cleavage, my thigh highs and sheer pink panties. I topped it all off with a pair of classy 3" heels. Overall, it was a bit more than I would normally wear, but not enough that it would raise any eyebrows.

I got to my class 15 minutes early, just enough time to finish my coffee and get my lesson plans squared away. It was near the end of the semester, so the days were getting easier. I teach AP Biology and since the AP test was last weekend, I took this time to teach current events and popular science as a reward for the students' hard work. The day was going well when one of my best students stopped by to ask for my advice.

"Mrs. B, do you think you would have time after school to help me decide which college offer to choose. My parents never went, so they haven't been much help. I would really like your insight since I feel like this is the most important decision of my life," he implored.

DeAndre, "Dre" for short, was our charismatic wide receiver. However, most of us liked that he broke the jock stereotype since he also captained the debate team, made class valedictorian, and volunteered at the local animal shelter twice a week. I always got along well with him and wanted to help him out, so of course I said, yes. I knew he wanted to focus on physical therapy so I decided to do a little research into his top schools. He really did have a tough decision, having managed to get a full ride to Duke, MIT, and Princeton.

Right after the final bell, Dre made his way into my classroom, shutting the door behind him and grabbing the first desk up front. It was spirit week, so all the doors had been decorated with school colors and other posters and flair effectively blocked out the windows. I considered opening the door but decided the hallway noise was too distracting.

Dre pulled out a notebook with his acceptance packages, and we formulated a game plan, making a pro/con list for all three schools. I had Dre name off a list of his top priorities and then helped him with some things he might not have considered, such as location, weather, and distance from family. We were really making some progress when I got tired of pacing back and forth and hopped up on my desk. As I scooted back to get more comfortable, I noticed that the lacy stocking top was peeking out. I'm not the only one who noticed.

I caught Dre checking me out, but he averted his eyes as soon as he saw me look at him. It was cute, like a kid caught with his hand in the cookie jar. The idea of this senior high school student trying to look up my skirt was pretty appealing to my ego, admittedly. But, of course, my new oversexed brain could not leave it alone. I would occasionally lean back so that my skirt would ride up to see if I could get Dre to look. Unfortunately, Dre was a polite teen because he would not look if he knew I was watching.

I did notice that he was becoming more flustered with the conversation. Since I knew I was getting to him, I needed to up the game somehow. I'm guessing it's because David brought it up in the hot tub, but my mind flashed to Basic Instinct. No, I can't do that, he's just a boy I tried to reason with myself. He's not a boy, he's 18, about to be an Ivy League college man. There's no problem with teasing him a little I thought, and technically it's not against any rules or laws I finally rationalized.

With that argument settled, I leaned back on my elbows and slowly uncrossed my legs and then re-crossed them on the other side. I caught him staring right up my skirt and his mouth was partially hanging open like a cartoon character. Could he see my patch of hair or my lips through the sheer material?

Oh my God, I forgot that I wore my sheer panties. I might be giving more of a show than I intended. Instead of freaking out, however, it turned me on even more knowing that he could potentially see my pussy. I gave it another minute, and then repeated the move this time going even wider on the spread and slower on the rejoin. Dre now had one hand in his lap and any pretense of his working was gone. I think I broke him.

I figured I could not just keep doing my leg crossing, so instead, I simply uncrossed my legs and let them dangle together. Slowly I moved them apart until I'm sure there was about a five-inch gap between my legs. Sure enough, Dre was again staring right at my pleasure zone, and now it looked like he had his hand in his jean's pocket.

Was he playing with himself? That got me flustered to think this very good-looking kid was getting off to the site of my panties and maybe more. I felt the wetness start to spread throughout my crotch. Then the craziest thought came to my mind: I need to remove these damn panties.

I jumped off the desk, surprising Dre who pulled his hand out of his pocket, blabbering about the pro/con list. I pretended that I needed some gum from my purse behind the desk.

"Would you like some gum Dre?"

"No thanks Mrs. B, I'm good."

As I was kneeling down behind my desk, I slid my skirt up my thighs and pulled off my soaked panties. It was not a simple task I assure you, but I got it done. I stuffed the underwear into my purse and made my way back to the front of the desk. As I hopped up again, I made sure to spread my legs wider than normal. It must have worked because Dre's eyes about popped out of his head. His hand went right back into his pocket.

I repeated my routine from earlier although this time I acted truer to the movie. After a while I really pushed the envelope and pulled one my legs up to my chest while I let the other hang off the desk. At this point I realized I wasn't even trying to be subtle anymore. Dre started to stand up which brought me back to reality.

"Stay in your seat," I commanded with more authority than I thought possible.

"Yes ma'am," he courteously replied.

I realized that I was in control of this situation, and I was going to make the rules.

"You can look, but you can't touch me, only yourself." I ordered.

"OK," he simply replied.

Once the rules were established, I played a game of flasher with my best student. Periodically, I would show him my butterfly, while he kept his hand in his pocket, watching me like a hungry lion. However, my only issue was getting no relief. I was literally teasing and torturing myself while Dre got to caress his cock. My pussy was drooling on my desk at this point,t so I decided that just a small touch wouldn't hurt. I pulled my skirt up a little more and found my love button with my hand.

"Mmmmm...yeahhhhh," I quietly moaned out.

"Oh my god," I heard Dre whisper.

I rubbed myself while making eye contact with Dre, watching him watch me. Occasionally I would glance down at his crotch, but the damn desk blocked it. Then I realized that I had never seen a black dick before, and I really wanted to.

"Take it out." I heard myself saying.

"What if someone comes in?"

"I guess that's a risk you are going to have to take," I reasoned.

"Fuck it."

I knew it was possible for someone come in. but that actually added to the thrill. I also knew that interruption were unlikely on a Friday afternoon. I heard his zipper come down and watched as he reached into his pants to extricate his throbbing cock. Without asking, he turned the desk side-wise so that I could see his black cock. It was a good-looking dick I thought. Not as big as David's I noticed, but more like the average of David and Chris. He was cut and the color of his shaft matched the head. The only noticeable trait other than the color was the curve. His cock had an upward arc to it that I had never seen before. I imagined what it would feel like rubbing my g-spot on each thrust.

I increased my tempo, and he matched me almost perfectly. I could tell that we were both getting close as our breathing turned ragged and desperate. As I watched him stroke his dick, I noticed how he twisted on the up stroke while gripping it tightly. As I watched, he suddenly grunted, and I watched him shoot long white ribbons of cum onto the floor. So much cum I thought and so much distance! The first few white ropes landed all the way by my desk. That sight sent me over the edge, and my orgasm hit me hard and fast. He managed to keep cumming throughout my climax, which I found amazing.

As we both came down from our lust filled highs the awkwardness settled in. Did I just let this student watch me get myself off on my desk? Did he really just shoot a load of cum all over the floor? My new libido was getting out of control. Dre looked at little embarrassed as he stuffed his shriveling black cock back into his pants.

"That was the most incredible thing I've ever done. Thank you, Mrs. B. Oh, and you can trust me. This will be our little secret," he grinned.

"I apologize for putting you in this situation Dre. It was wrong of me. Please don't think of me any differently," I begged.

"Phshh. If anything, this makes me think more of you Mrs. B. I can promise you; this will stay between us," he promised again.

"Obviously, this would be bad for both of us if it got out. Besides, if it does get out, this will definitely never happen again," I said foolishly.

Did I just insinuate that this might happen again? Damn it, why I couldn't I just keep my mouth shut? I managed to get everything cleaned up and my panties back on. Chris would be just a little suspicious if I came home without my panties. Oh, we did finish the pro/con list because I do care about my students. We both thought MIT would be the best choice for Dre. I am sure its proximity to the high school had nothing to do with it.

Chris

I had such a good time after my little session with Claire that I was on cloud nine the rest of the week and with a permanent smile on my face the entire time. This state translated into my work because I was killing it at the office. A few employees even asked if something great had happened to me recently. Of course, I couldn't exactly tell them I was fucking my friend's wife in her ass, so I just gave the typical response of "nothing really, just feeling good." Lucy also seemed to be in high spirits lately, so I decided to use the gift card my office got me last Christmas. I typically avoid massages for some reason, but my plan had always been to use it for a couple's massage to get me some brownie points from Lucy or maybe get her in the mood. After that night in the hot tub when she was showing David half her ass, I thought maybe this could be a solid gold opportunity for sex.