Guess What I Saw? Ch. 03

"Really?" I interjected. "Your church is really that strict?" I knew next to nothing about her religion's tenets, other than the fact that they were very conservative in many ways.

"Tony, that's not really the point," Monica said, sounding a little bit peeved. "It's none of our business, anyway. But Kelly, sweetie, you're just rationalizing, aren't you? I mean, if you want to abide by your church's rules, shouldn't you avoid sex all together? I can't tell you how to live, but it seems to me you are just trying to skirt the rules. I don't mean to sound parental, but don't you think you'll feel bad about that?"

Kelly's explanation of her religion's rules, and how people followed the letter of them and that was it, was eye-opening. She was clearly very devout in her own way, and firmly believed she wouldn't be able to marry if she wasn't technically a virgin, and was very worried about getting into heaven. But she seemed to have no compunction about finding a workaround to the rules. She said the rules weren't made for us to understand or to speculate about their meanings -- that would show pride and hubris, which were sins. People were just intended to follow them. That was her stance, and she seemed unshakable in it. If she was taught that fornicating before marriage was a sin, and fornicating was defined as vaginal sex, then Kelly was comfortable enough doing anything else without fear of retribution, at least from God. Her parents were another matter.

I was so surprised by this conversation I hardly knew what to say. I couldn't fathom having a set of rules and simply following them without thinking about them. I was also quite surprised to find that she really cared so much about her religion. I had just assumed she was a black sheep and broke the rules as temptation won out, like everyone else I know.

I won't bore you with the rest of that conversation. It turns out Kelly's parents were much more conservative than the church required, at least in Kelly's opinion, so my idea of a rebellious black sheep wasn't so far off. It was just her parents she rebelled against, not her church. It was fascinating to learn so much more about this young woman and how she thought, but I don't know if it is germane to my story, so I'll move on.

Anyway, I know the part you really want to find out about is the sex, right? Yeah, that's what I thought.

If you think we ended the night with a wild orgy replete with butt-fucking, three way sex, lesbian interludes, and cum play, you'd be wrong. Sorry.

All that came later.

We ended the evening with an agreement Kelly would visit over the weekend and I would teach her what I could. Kelly's boyfriend was busy, and I was free, so it seemed a perfect opportunity. There was still a tentative air about the whole thing, and I for one wasn't at all sure much would happen, but we wanted to explore it further. We laid a few ground rules, as well. The biggest one was no more secrets among the three of us. How to handle Dylan's role in all this was a bit stickier. Kelly insisted that he not be told anything about her adventures and experiments with me. I had serious misgivings about that part of it, both for Kelly's sake and Dylan's, but she was unshakable, so we agreed.

Honestly, I was worried about the idea of anal sex with Kelly. I'm not gonna lie, I wanted to do it, and I was already picturing it in my mind's eye, but I was really afraid it would hurt her a lot - at first, anyway. Now, I don't have a giant cock by any stretch, maybe slightly above the average size, but who knows that kind of thing for sure? All I know is, Kelly is tiny. I mentioned before that she is athletic, so she is lean and strong, but she is probably just a little over five feet tall, and if she weighs 95 lbs I'd be surprised. While her little ass is tight and perfectly rounded, her hips are narrow. The image of my cock disappearing into that slim little body turned me on enormously, but I was apprehensive.

Monica and I talked about it more when we went to bed that night. We agreed that not telling Dylan was a bad idea, but we also both knew that he would probably break up with Kelly if he knew, so we reluctantly accepted her choice. We decided to try, just once more, to talk her out of this, to try to get her to experiment with Dylan instead of me. It was the grown-up, parental thing to do, even though we weren't her parents. But we both were well aware that we would probably go through with it if Kelly insisted.

Christ, it was like waving a crack pipe under an addict's nose. I'm only human after all, and it's not very damn often a 50 year old man has the opportunity to dally with a sexy 18 year old. As in NEVER. And my wife was complicit, however reluctantly. There was no way to say no.

We lay quietly in bed, but I sensed Monica was as restless as I.

"My god, Tony," Monica murmured as she propped herself on one elbow, "I can already imagine you bending her over and fucking that tight little ass." She reached over to my side of the bed and lightly caressed my awakening cock. She leaned over and kissed my jawline and nibbled my ear as she spoke. "It's pretty damn hot." Her hot breath in my ear brought on a full-fledged raging boner, which she began to stroke through my underwear.

One thing led to another, and soon Monica was gobbling my cock hungrily. She could read me like a book, and always seemed to know when to tease, and when to go for broke, and how to make me ride a roller coaster of sensation. I couldn't help but to compare her to Kelly, though I felt awful about it. With Kelly, there was such an exciting newness, and of course the situation was mindblowing. Her technique was also amazing for someone so new to it. Here was Monica, though, sucking me as if she could feel what I was feeling, as if she knew exactly what I wanted and needed. There was a connection there beyond the physical, and I realized I had begun to take that for granted after so many years of marriage. I was overwhelmed with emotion, and I was kind of glad she couldn't see the tears on my face.

I pulled her body on top of mine so I could lick her as she sucked me. As soon as she realized what I was doing, she happily helped out, straddling my face to give me access to her moist, fragrant slit. I devoured Monica's sweet pussy with abandon, her excitement flowing into me with her juices. I probably would have cum within minutes, had she not known when to back off and tease, or change up what she was doing. I, on the other hand, couldn't wait to feel her gush all over my face. I licked and sucked and toyed with her clit until she was shuddering on top of me. She lifted her head and arched her back as a high moan of pleasure crescendoed, ended in a rush of released breath and cries of ecstasy as she orgasmed. I was in heaven between her legs, with her hips grinding her pubis against my face in the throes of her release.

Monica leaned over a grabbed a bottle of lube from the nightstand, and slathered some on my rock hard shaft before straddling me again in a cowgirl position.

As she lowered herself onto my cock, she said "You haven't fucked me in the ass for a while. I think you need some practice if you're gonna teach Kelly anything!"

I felt her guiding the head of my lubed shaft into her tight, tight asshole. She yelped a little and paused as her body adjusted itself to my invading member before lowering herself gradually.

"Oh my god. I'd almost forgotten what this was like. I remember our first time..." She paused to breathe deeply, lowering herself a little more. "Do you think she can handle it, Tony? She's so little." She let out a deeply held breath as she finally lowered herself onto my full length. "Oh my god!"

She moved atop me, and I plunged myself in and out of her ass in long firm motions. I like to feel every inch of my cock slide past the tight rubber band muscles of her ass. If you go slowly enough, you can feel the second sphincter just a couple of inches up from the anus, and then slight curve where the rectum joins the colon. It's such an amazing symphony of physical stimulation, and even after all these years there is still something just a little bit taboo about it. The fact that anal sex is much more commonly accepted has done nothing to diminish the excitement for us. Monica reached down and rubbed her clit with her right hand and tugged at her nipples with her left as she rode me.

Five minutes later I felt myself climbing toward the brink and then rocketing over the edge as I unloaded my cum deep within my wife's ass. She knew I came, but that didn't slow her down at all -- she was very close to another orgasm herself.

Moments later, Monica peaked in a second gushing climax, wet juices flowing over her fingers and my belly. She sat down hard on my cock and tugged viciously at her nipples as her fingers deftly eked the last sparks of electricity from her swollen clit, prolonging her orgasm as long as possible before stimulation turned to irritation. Even after she had finished, she sat atop me, gently rocking and rubbing her hands on my chest. The feeling was just enough to keep me hard, and I enjoyed the fact she wasn't in any hurry.

At last she spoke, almost in dream, it seemed. "Tony, I'm jealous..."

"No, baby! Please don't be jealous. I won't go do it if it bothers you."

"No, Tony, it'll be OK. I agreed, after all.."

"But Monica!"

"No, I said it was OK. And the truth is, it really turns me on to think of it. I'm just torn. She's so young and pretty, Tony, and I'm..."

I put my finger to her lips. "You, Monica, are the sexiest, most beautiful, most understanding and passionate woman I know." I paused to let her know I was serious, then I couldn't help but lighten things up by adding, "So shut your pie hole!"

She laughed and layed forward against my chest, resting her head against my shoulder. I kissed her hair and held on to her.

"Hey, I have an idea," I mumbled. The thought had just occurred to me, and I wasn't sure how to present it. "What if we, you know, ask her if you can be there. Um, maybe you could join us. You think? I mean, she said she sometimes thought she might be a lesbian or bisexual, soooo, I don't know..."

Monica turned and looked at me. "No shit!?"

Her smile made my night.

"No shit! Now, let's get some sleep."

Saturday morning couldn't come quickly enough, and when it finally arrived, Monica and I were like kids at Christmas. We still hadn't asked Kelly if Monica could join in, but I was 99% sure she would agree. Monica and I chattered all morning, and we couldn't stay away from the topic of our impending tryst. Monica came up with a great idea, too. She suggested we offer to take Kelly to Adam & Eve and get some anal toys to ease her into things. It was fantastic talking about this stuff in the open. I was afraid the excitement would be diminished, but it actually seemed to be amplified, sharing the experience with my wife.

When Kelly arrived, she was more than happy to have Monica join us, and seemed really excited about the toy shopping, too.

She even suggested bringing my camera, too. "Who knows, maybe we can have some fun while we're out!"

I had almost forgotten about our little neighbor's exhibitionist streak. My cock was hard before we got in the car.

On the drive, Monica explained the thinking behind the toys, telling Kelly that the first time trying anal sex was often painful, and the toys might help ease that a little bit. Kelly seemed really excited by the idea of Monica using the toys on her, which led Monica to broach the topic of bisexuality. I listened with baited breath as they talked.

"So, Tony mentioned that you might be interested in trying a little lesbian stuff. Is that right?"

"Oh, yeah!" Kelly giggled nervously. "I kind of forgot I told him about that. I've pretty much decided I'm not a lesbian, but I might be bisexual, I think. I love licking my fingers after playing with myself. But I also love sucking Dylan's cock, and the way he shoots his cum in my mouth. How about you, Mrs. Mac? Have you ever, you know, been with another girl?"

It was Monica's turn to giggle nervously. "Um, call me Monica, Kelly. Please. No. I, uh, I've never been with a girl. I never really thought about it."

Kelly looked a little disappointed as I glanced at her in the rear-view mirror.

Monica was turned in her seat, talking over the seat back with Kelly, and saw the look, too.

"I never thought about it before," she quickly added, not wanting to disappoint Kelly, "but I have sure been thinking about it a lot since Tony mentioned it."

They laughed and continued talking until we arrived at the store. I was excited to hear a lot of flirtation and double entendre in their conversation. My hard-on was starting to feel like a permanent fixture, and I had to rearrange myself in my shorts as we got out of the car.

Of course, Kelly had never been in a sex shop at all, and she was thrilled by the variety of toys, lingerie, videos, and potions for sale. She wore a clinging navy babydoll tee with spaghetti straps and the tiniest pair of white shorts I'd ever seen. It was funny seeing the other customers watching her mess around with the various dildos and vibrators, accompanied by a couple who looked old enough to be her parents. Some looked on with obvious lust, while others seemed puzzled or disturbed that we had taken our "daughter" to a sex shop. I whispered as much to Kelly and Monica, and was delighted to see a mischievous gleam sparkle in Kelly's eye.

"Let's mess with them!" she grinned gleefully.

She grabbed a double-ended purple dildo from the wall, and held it up in its blister pack. She held it up next to her face and opened her mouth wide, as if gauging how deep she could take it.

She stepped next to Monica and said "Do you think we could meet in the middle?" She held the huge dong between them, and they each made the motion of gliding their open mouths toward the middle, and much to my surprise they met in a tentative but incredibly hot kiss! My heart beat hard in my chest, and I looked around to see they were getting quite a bit of attention.

I am not really easily embarrassed, but I could feel my face flush at some of the things Kelly and Monica were saying. My wife has never been a prude at all, but I never in a million years would have imagined her flirting in public with a woman, much less a woman less than half her age. She was really into it, though. Now that the dam had been broken, she was having fun riding the rapids.

I was feeling turned on beyond measure. My cock was so hard it was uncomfortable in my shorts, and I was a little disconcerted that the bulge was so obvious.

I noticed some of the other shoppers cleared away in embarrassment, but a fair number of them seemed to have become very interested in the racks of toys and videos that were near us.

Kelly moved over to a display of butt plugs in every color and size imaginable. She picked out a clear model that was about 4 inches long and about 1 ½ inches in diameter at the widest part. She held it up to show me her choice.

She waited to make sure she would be heard by the strangers around us, and then said in a loud but enticing voice, "Do you think, if can take this plug up my ass, I can handle your big cock, Mr. Mac? I know it's not as big as you," she cooed, lightly rubbing my straining fly, "but maybe I could work my way up."

I thought I might die of embarrassment, and I felt eyes on me from all quarters. Just like the time Kelly kissed me on the street, some of the looks said "you lucky fuck!" and others clearly conveyed "you dirty old bastard!" Nevertheless, none of them could hide the desire and excitement behind their stares, not even the disgusted ones.

Monica eased up to us and held up her most recent discovery -- a strap-on! It had a harness to fit around her hips and featured a smooth, slender dong about five inches long.

"I thought this might be fun!" she beamed, showing us the new toy. In a more conspiratorial voice she said, "I kind of want a chance at that little bottom, too!" She surprised me by reaching down and grabbing Kelly's ass, tugging her close so that their hips were touching and they were face to face. I saw her fingers cupping that small, round ass-cheek and fiddling with the edge of the white material. Kelly's nipples stood at attention, straining against the tight knit material of her babydoll, and the way they looked at one another, I thought they may kiss again.

Unfortunately, the moment was broken by the clerk coming over and saying tactfully, "Is there anything at all I can help you with?" Her voice was retail-cheerful, but her look said "Knock it off!"

We had found everything we came for and more, so we took our selections and accompanied the clerk to the checkstand. As we payed for our goodies she looked at us a bit wistfully and said, "Sorry about that. It was actually really fucking hot, but my manager wants to keep a tight rein on that stuff. We're supposed to be a family sex toy store." She shook her head at the irony. "I guess that's what you get when you work for a corporate sex shop." She grinned a lopsided smile and said, "Have fun."

I'm quite sure I detected a bit of longing in her voice.

We decided to grab some lunch, and Kelly reminded me we hadn't taken any pictures yet. I asked her what kind of pictures she wanted to take, but I was pretty sure I knew the answer, after out last photography outing. The only surprise was that she wanted me take some pictures of her and Monica fooling around a little in some public place!

Monica balked at first, saying she was too old to get arrested for indecent exposure. Kelly teased her a little, saying the chance of getting caught was part of the excitement. This kind of got us onto a discussion about how Kelly came to be such an exhibitionist. I was a little ashamed when she told me it all started the first time she caught us having sex on the couch. She was so excited by the sight, she wanted to do that, too. She was turned on by giving someone else a thrill. I felt like I had contributed to the corruption of a young person, but she reassured me it was all her decision. She was quite sure her family thought she had the devil in her long before I influenced her.

I thought again about how brave she must be to do these things that were so outside her family's norm. And she wasn't doing them just to rebel. She loved and respected her parents, and had no desire to upset them, but she wasn't going let them decide how she would live her life, either. I wondered briefly how the duality of her life would be resolved, but I realized I couldn't be the one to make her decisions for her.

We were eating lunch in relative calm, just enjoying getting to know one another better. Monica was still iffy about the photographs, so she quizzed Kelly a little more about what she had in mind.

Kelly took a quick look around the restaurant, and quick as a flash slipped the spaghetti straps down her shoulders and pulled the babydoll down below her breasts. Monica gasped as Kelly began to giggle and play with her nipples.

"I was thinking something like this!" she answered, a happy, impish grin spread across her face. We could see the backs of other diners' heads, but no one was looking our way. "Except," she continued, "I thought maybe you should be the one rubbing my nipples..."

With that she took Monica's hand and placed it on her breast.

"Oh my god, Kelly!" Monica breathed excitedly. She fumbled awkwardly with Kelly's small breast and pert pink nipple, fear and adrenaline making her hand shake clumsily.

Ever the helpful one, I said in a stage whisper, "Go ahead, I'll keep a lookout!"

Monica shot me a look that said she wanted to choke me, but the look was belied by the hungry lust I also saw on her face.