Pegged by Married MILF from Church

*Though this story contains no actual guy/guy action, it is mentioned. All individuals are involved are over the age of 18. Story contains mild blasphemy*

"Been a couple weeks," the extremely attractive woman sitting across from me said. She was quietly nibbling on a slice of cherry pie. I for my part was doing the same with a piece of pumpkin pie.

"Yes it has," I said. Truth be told, I had been avoiding her. She was almost forty, with all the good that came with age and none of the bad. There's not been many women I've been as attracted to as Lana. That being said, she was married with two kids and I wasn't even going to think about the possibility. Of course, when your family drags you to a church pie social, not knowing the true reasons you had been avoiding all church events for about three months it gets harder to avoid them.

"So where's the rest of the family?" I asked, trying to make conversation without giving away the wanderings of a young mind.

"They're in Connecticut for the weekend," she said, sounding vaguely irritated and relieved at the same time, "seeing Gabe's parents."

"And you're not with them because..."

"Because the last time I went to Connecticut and saw Margaret and Dave they pulled me aside and gave me the business card of a divorce attorney," she said with a sigh, I don't need that kind of negativity in my life."

"Hell's bells," was all I could manage to say, "and I thought my family hated each other."

"Oh well, I have the house to myself for the weekend." She said, taking another bite of her pie.

"That's always nice," I said, "a little 'me-time' goes a long way."

"So what does a young buck like you do when he's home alone?" she asked, "Play video games? Blast that loud rock music I always hear when your car pulls into the church?" she leaned in conspiratorially "bring girls over?"

The sound I made when she said that could best be described as a squeak. Were she not who she was I would have laughed, but being none other than who she was the question caught me off guard. "Uhh, not so much on the last one, but definitely on the first two."

"Oh come on," she said, "I'm not some old church lady, or your mom. You don't need to play the good boy for me."

"I'm not playing," I said, "I'm not exactly a good boy either, I just have rotten luck with women."

"How so?" she asked.

"Oh you know, being attracted exclusively to crazy and/or married women." I said without thinking, and then realized what I had said.

"You see now that is a problem," she said "but it doesn't have to be."

"What do you mean," I said, not sure if I hoped she was going to go there, or hoping she wouldn't.

"What exactly is the crazy you refer to?"

"Well for example, there was this girl I met a while back. She was hot and pretty buff, which I like, and we hit it off and went on a few dates."

"So when does the crazy come in?"

"Well one day we were texting and things got a little, uh, spicy."

She laughed a low, almost malicious laugh, "How fun."

"She mentioned, almost passingly that she wanted to..." I stopped, not sure if I wanted to share the next detail.

"Wanted to what?" she asked.

"Uh, do you know what, uh, pegging is?" I asked. She got this weird look on her face when I asked, almost scared or maybe disappointed.

"Yeah, I don't know if I'd call that crazy."

"That's not the crazy," I said. Truth be told I was totally down. The whole idea had sounded hot, it was the other stuff that made me uncomfortable. "I said I might be willing to try it and she got excited. Then she started talking about other stuff like..."

"Like what? Bondage?"

"Worse, apparently she had a thing for..." I trailed off before figuring to hell with it, I've said this much, "guy on guy action. Apparently she was already sleeping with her roommate, and apparently she had fantasies of him, uh, joining us," I said as I sipped on my water, suddenly a bit uncomfortable.

She covered her shocked expression with her hand as her eyes darted to the side. I think she may have even been blushing. "Well then, I can see what you mean about the crazy."

"That's probably the best example of the kind of crazy I attract," I said, which was true enough.

"So you like buff women huh?" She asked, apparently changing the subject.

"Yeah," I said, "there's just something about, I don't know what but..." I trailed off. She was wearing a red sweater and usually did. I found out that underneath she was wearing a black tank top. As she took off her sweater I got a peek at her midriff and visible, if not distinctly chiseled, abs. She then began showing off her muscled arms, giggling at my obvious surprise.

"I know I wear a sweater most of the time, but hey all this work someone has to appreciate them." I said nothing and tried diligently to avoid staring. She was gorgeous. Her arms didn't exactly bulge out or anything but she had definite biceps and shoulders. Her neck was gorgeous, and pale skin flowed from the nape of her neck down the front of her chest. Underneath the tank top her breasts threatened to steal the show. They weren't massive by any means but they were nothing to sneeze at.

"Furthermore," she said, her eyes boring directly into my soul, "I saw the look in your eyes as you said you 'might' be interested in being penetrated by that girl's big, hard, strap-on penis." I looked around, hoping to God no one was hearing, "I don't think you were just open-minded. You found the idea as hot as she did." Her words were low and heavy, squeezing around my torso and making my breathing tight and heart rate high. "Didn't you?"

"Now just what are you getting at?" I managed to say, my throat dry.

"I have the house to myself all weekend, and I have a boy who's eager to try what my husband isn't willing to," she said before leaning in even further and adding "what the hell do you think I'm getting at?"

She leaned back and gave me a look of marked prey. I guess that's where the term cougar comes from. Apparently her house was a short walk from the church. Within a few minutes we were just inside her door mauling each other. She quickly kicked off her shoes and I could tell she wanted me to do the same. Adultery is one thing, but tracking mud onto her nice carpet? Shameful.

We went from horizontal to vertical pretty quickly once we got to her couch. Her sweater came off once more, along with her shirt. Her red lace bra was bright compared to the pale skin underneath. "I picked it out just for you," she said. She had planned this out, maybe not all of it, but I was marked before I even sat down. God just the thought of that made me so much hornier.

Soon enough though the bra was off and I slowly began kissing my way down from her mouth to her neck, eventually finding my way down to her bare breasts. Eventually I moved my way on down her torso, across her very nice abs and to her crotch. She stopped me as I began to unbutton her black jeans. "Not here," she said.

She led me up the stairs, still topless and disappeared into her bedroom. I followed, diligently avoiding glancing into the room next to hers, which from the peripheral view of a bunk bed certainly belonged to her kids.

She didn't so much fall onto the bed as she did pull me onto it on top of her. I resumed where I was on the couch and began unbuttoning her pants. Her panties matched the bra which had been left downstairs, but quickly came off with her pants.

My mouth began exploring. I was not exactly experienced at this, but I did my best. Eventually my tongue found a little know that made Lana moan, which I had to assume to be her clit. I continued flicking my tongue back and forth against it, starting slow occasionally pressing down, occasionally backing off. Eventually I found my rhythm if my tongue did eventually start getting tired.

"Fuck me," she said. She hadn't climaxed yet, but I wasn't about to argue.

"Protection?" I asked. I did not want to risk anything given the circumstances.

"I'm on the pill, and clean now get your ass over here and fuck me."

I lined myself up at her entrance, holding off for a second, wanting to feel her squirm under me. Instead, she grabbed my hips and pulled me into her. It was almost violent, but the way she moaned I could tell she enjoyed it. I picked up the pace and began moving in and out.

Her moans quickened and became louder. I moved in to begin kissing her again and she kissed me back, frantically this time. Her breasts pressed up against my chest as I moved, pace quickening slightly.

"Harder, but don't you dare cum yet." Very well, I continued even harder this time. What were moans before transformed into short gasps and whimpers. I could feel her tightening around me as she finally screamed once and came.

I found myself internally reciting the lord's prayer in an attempt to hold myself back. Sure it was probably sacrilege but it did the trick. By some miracle I managed to hold back from cumming. She pressed a hand against my chest and I backed out. I really wanted to cum, but I also really didn't want to disappoint her. I also knew that once I came I was going to be a lot more rational and screw that noise.

She stood up and walked towards her closet. She walked like a woman who had just got fucked, but she walked with purpose. She reached her hand up to the top of her closet and pulled down a shoebox, which contained a strap-on penis and a bottle of lube. I could kind of sympathize with her husband not being into it, the damned thing was huge.

My cock was not exactly unimpressive, and it sure as hell did the job for her, but the strap-on was bigger. It wasn't exactly insane, or insurmountable, but it had me beat by at least two inches in length and a half inch in girth. She put the harness around herself and in an amount of time that had to be practiced she had a large, impressive cock sticking out of her hips.

She sat me down on the bed, and gently pushed me until I was on my back. She knelt down and instead of taking my cock into her mouth, she instead began tonguing my ass. She didn't even touch my cock. Being as horny as I was I nearly succumbed to temptation but she pushed my hand away from my own cock, bidding me to focus on the pleasure coming from the rimjob she was giving me.

After a while of getting me to relax my asshole she pulled out her bottle of lube and began applying it to my asshole, working around before eventually sticking a finger inside me. It started off as just one knuckle, going inside before traveling around the outside, then two knuckles, then her whole finger.

Finally she stuck a second finger in and the discomfort started. No pain, but discomfort. I gasped and she slowed her pace, returning to one finger. She added a second again and this time it felt natural.

Before I knew it she pronounced me ready to go and began lathering up her cock placing it at my entrance. "Don't worry baby I'll go slowly," she said slowly pressing against, but not yet into me. She was waiting for me to relax and once I did I felt her cock parting my asshole. I gasped in surprise and she stopped. "Are you okay?"

"Yes, keep going," I said with more confidence than I felt. She did. I felt as the head worked its way all the way into me. She stopped for a second, waiting for me to get accustomed. Rather than verbalizing anything this time I simply nodded for her to continue.

After reaching what felt like about halfway she pulled back just a little. The feeling as she did was a bit uncomfortable, but nothing too intense. Then, in a little bit further than last time. We continued like that for a while until she had, somehow, managed to hilt herself inside of me.

Soon she began moving back then all the way in again. She was properly fucking me, but still very gentle. After a few moments of that pace she eventually pulled out almost all the way and then all the way back in. That was when I discovered that, yes, the stories of the kind of pleasure men get from having their ass fucked was real.

The tingling sensation started in my ass and began to radiate. It moved through my cock, but was not of my cock. I moaned, quietly, but she still heard it and took that as a go ahead to continue that. She did it again, and it was just as pleasurable, then she began fucking me a bit faster, not all the way in or out, but good medium length strokes, with similar radiating pleasure each time.

"Yes," I found myself saying as she fucked me, still very gently, "you can go a little bit harder." Boy she did not hesitate after I said that. What was once a gentle lovemaking, albeit with roles reversed, was now a hard fucking. Not rough, or overly intense, but harder. I felt the shockwave every time she hilted herself in me. The shockwave added to the pleasure almost as a separate source of pleasure. Over and over she smacked into my ass, such that I was now on the verge of orgasm.

"Harder," I said again, and she responded in kind, now pounding my ass. She was clearly taking pleasure in this too.

"I want you to cum with your ass," she said, "I can feel how close you are, I can hear your whimpers, I can see the precum leaking from your cock." She was right, but it still felt like an invisible wall, a tangible pleasure ceiling. "Yeah you like my cock don't you."

"Yes Lana,"

"You wanted this. You've been wanting this for a while."

"Yes."

"Maybe one of these days you'd want to try a real cock in your ass," the idea didn't excite me before, but now the idea of Lana arranging for me to have a real cock fuck my ass was threatening to send me over the edge. I didn't say anything.

"Maybe you'd like for me to get reinforcements, have someone on the other side fucking your cute little throat." Oh God, the thought of that.

"Oh yeah you'd like that. Have another guy here with a real cock and me with a strap-on. Now, where would you want the real cock to finish?"

"What?" I asked, not sure what she was getting at.

"Would you rather have me back here fucking your ass while some other hot stud unloaded into your mouth, or would you want me to take my cock out of your ass, and push it into your throat while he fucks your ass and gives you a nice creampie?"

My cock was now leaking more than I think it ever had. The muscles around my ass were spasming, clenching down to pull the cock into me then trying to push it out, both motions doing nothing but press my prostate against her relentless cock.

"I...I don't know," I said, not wanting to verbally admit to how much the thought was turning me on.

"In that case I guess it's my decision, and much as I'd like to see you get creampied I don't wanna give up this ass," she was fucking me harder, with total abandon as her own orgasm approached, "So I'd let him continue fucking your throat, but have him pull out at the last second,"

I felt my own orgasm building.

"Start stroking his cock while I continued to fuck you,"

"Oh god I'm gonna cum, I'm gonna cum with my ass!"

"We could both watch as he came all over your face," and on that thought we both came. She trembled as if something was fucking her, and I felt my whole body shake as cum began to steadily leak from my cock. Sure I had experienced some powerful orgasms, but they never held a candle to this. She leaned in and kissed me as our orgasms subsided.

"Hey," she said as we came down, "that was just talk okay."

"I know, but it turned me on so much."

"I know."

After a while we were both dressed and arriving back at the church separately. It would appear that no one noticed our absence. She pulled me aside right as I was about to leave and said "what happened tonight, and what will continue to happen," she looked at me with that same 'marked' look, "stays between us."

I nodded in understanding.