Guess What I Saw? Ch. 05

I think this will be the final chapter for Tony, Monica, and Kelly. But are our voyeurs and exhibitionists being watched? Hope you enjoy this chapter!

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Hi again. I am so sorry for leaving you hanging last time. I PROMISE I'll tell you all about the rest of our afternoon this time.

Well, when I last left you, Kelly (my hot 18 year old neighbor), Monica (my hot 50 year old wife), and I had just gotten back from buying sex toys and taking pictures, all of which was a prelude to fulfilling Kelly's request to introduce her to anal sex. (She wants to "technically" remain a virgin so she can get married in her church one day, remember? Craziness, I know.) When I left off before, Kelly was emptying the bag of sex toys and opening them up like a kid at Christmas. We washed them all thoroughly and then got down to the hard work of deciding which to try first.

Since Kelly had jerked me off into Monica's mouth on the way home, I was feeling a little spent. Seeing the girls mess with the toys had my cock showing signs of life, but I was content to just watch and recover for a while, sipping my cool drink.

They settled on the first toy they had messed around with at the store, the double ended dildo. It was a clear pink color, and the package said it was 18 inches long. It looked every bit of it, too, especially compared to Kelly's petite body and face. I had little doubt that the girls could make good use of it, though.

Monica took charge and held the dong up to Kelly's face. Kelly opened her mouth with an air of sweet surrender, letting Monica know with the subtlest of expressions that she could do with the dong whatever she wanted. Holding it near the middle, Monica slid it between pink, waiting lips, moving ever so gently and slowly. I found myself instantly on the edge of my seat. I really wanted to see how far down her throat Kelly could take it, but I was forced to wait as Monica slowly and tenderly slid just a few inches of it in and out of Kelly's mouth. I could see saliva glistening as it coated the pink dildo and wet Kelly's soft lips.

Both women were standing, Kelly naked and Monica still fully dressed, not that she was dressed in a lot. Her underthings had been ditched earlier, but she still wore her button-down blouse and her skirt. I think I might have moaned a little as Kelly slowly sank to her knees, kneeling in subservient, naked glory before Monica. There was just something amazing about seeing my wife in such an implied position of power over my sweet sexy neighbor.

Monica must have inferred that Kelly was willing to take much more, because she began pumping the double dildo deeper into her mouth. My wife could never be called cruel or even forceful, but Kelly's overt surrender brought out an aggressive side to her I had never seen before. I have to admit, it turned me on immensely. Kelly instinctively folded her hands behind her back and looked up at Monica, practically begging her to force the dildo down her throat, to test her limits and see just how much she could take. As I said before, my dick isn't tiny by any stretch, but soon my wife was sliding well over half of the dildo down Kelly's throat, maybe ten or eleven inches - several inches more than I could ever give her. I was amazed that she could allow the shaft to penetrate so deeply without gagging much at all. I could see the dildo expanding her throat and causing her runner's veins to stand out with each deep thrust, and my poor cock strained against my shorts once again, torturing me with the pleasure of a full raging hard-on.

Saliva dripped down Kelly's chin in glistening ropes, and after a good ten minutes of fucking her mouth with the dong, Monica stopped and then bent to lick and kiss the wetness from her face. They kissed for several minutes, Monica bent to Kelly's upturned face, her hands caressing her bare, hard nipples and small firm breasts.

They were driving me CRAZY again. I loved it!

Monica knelt beside Kelly and started sucking on one end of the double dildo. Kelly caught on right away and started sucking the other end. Monica held the shaft firmly in the middle with her fist, and for a while neither woman made any motion to deepthroat or anything, they just slowly gave head while looking into one another's eyes. Gradually they started going deeper and deeper until, with each stroke, they touched Monica's hand with wet lips. Soon Monica released her grip entirely, and they moved toward one another's faces until, amazingly, they met in the middle. Monica wrapped her hands around the back of Kelly's neck and began controlling the motion, drawing them apart and then back together, meeting in the middle for a kind of open-mouthed kiss, with the dildo wedged down each of their throats.

Then Monica gripped her end of the dildo between her teeth, with only a few inches in her mouth, so that an enormous length of dong protruded, and she began to fuck Kelly's mouth this way, her head bobbing as she slid the pink shaft into the wet, pink, acquiescent "O" of Kelly's mouth. After a few minutes of this, probing deeper and deeper all the time, she finally found Kelly's limit - not that it seemed to bother Kelly, really. It was just that the dildo would fit no further. I saw the smallest of spasms ripple across Kelly's torso as she suppressed a gag, but that was it. Still, she had to have fit at least 11 or 12 inches past her lips. I was gripped with lust and amazement.

"That's it, you're the champ!" Monica joked as she set aside the dildo and caught her breath. "I don't know how you can do it."

"Me either," Kelly giggled, almost shyly.

Monica stretched like a cat and said, "Anyone who can deepthroat like that deserves a good orgasm." A pensive look came over her as she continued, "I've never gone down on a woman, so I don't know if I'll be any good, but I'd love to taste you..."

"Please do, Mrs. Mac," Kelly answered almost before Monica had finished speaking. "I'm sure you'll do great!"

Monica stood and helped Kelly to her feet. She quickly stripped out of her skirt and blouse before hugging Kelly close and kissing her deeply. The sight of my wife's tall, tan form against my young lover's pale, compact, athletic body cause yet another surge of adrenaline. All that beautiful skin!

Monica layed Kelly down on her back on the plush carpet, illuminated and dappled in the bright checkerboard of sun that shone through the framed windowpanes. She knelt and gently spread Kelly's thighs and nestled between them. Her dark hair spilled in a cascading fan over Kelly's smooth white stomach as she kissed all around the already-glistening labia, tonguing those magical hollows between pussy and leg, and using her fingers to probe the clitoral hood. Finally, with a deep moan, she let her tongue slip into Kelly's hot, wet little slice of heaven. Then, both women were moaning as Monica licked and slurped, gaining confidence with every flash of her tongue.

I couldn't take any more watching, and stood to take off my clothes. I started to move in behind Monica so I could fuck her from behind as she ate Kelly, but as I tried to lift her hips a bit, she shooed me away.

"You already got off, you greedy thing! Besides, you've had her to yourself long enough -- it's my turn!" she teased. "Now go sit back down!"

Thus chastened, I went back to my seat, absentmindedly stroking myself as I watched the incredible show in front of me.

Monica plied her tongue with focused intensity, and soon Kelly was writhing as her muscles rippled with the pleasure flowing through them. She grabbed Monica's hair and pulled her face hard into her wetness. Bucking and moaning, Kelly rode a wave of fire into a huge orgasm, crying out and wrapping her legs around Monica's neck in the throes of it's grip. Monica didn't pause for a moment, and I could hear the wet slurping sounds as she lapped up the flood of sweet juices flowing from Kelly's tiny pink flower.

With only a moment's pause, Kelly was up and kissing Monica's dripping face, tenderly sucking Mon's bottom lip into her mouth and probing with her tongue.

"Again?" she asked plaintively. "Please!"

Without waiting for a reply, she eased Monica onto her back and then straddled her face. If the sight of Monica stretched between Kelly's legs was hot, the sight of Kelly riding my wife's face was fucking unbelievable. She swiveled her hips with lithe grace and ground her pussy onto Monica's furiously working tongue. Monica reached up with both hands, holding onto and caressing Kelly's tight ass and hips. It was hypnotizing, watching the smooth, flowing symphony of movement as Monica's full breasts moved and swayed with the motion of Kelly's hips. As if she knew I was thinking about breasts, Monica moved her hands up Kelly's body and began to rub and tweak the tiny pink nubs of her nipples, which stood proudly atop the small smooth mounds of her breasts. In much less time than it took for her to get off the first time, Kelly reached another orgasmic peak, crying out "Oh, oh, oh, ooohh!!" as her body shuddered and shook.

After her climax subsided, she climbed off her perch and snuggled with Monica to catch her breath for a few minutes. I let them be calm and peaceful for a while as they shared a bond of mutual pleasure and exploration. The sunlight had shifted across the carpeted floor, and now only their intertwined legs were illuminated by its warm golden glow.

I soon found myself stroking my cock again and raring to go. I couldn't wait any longer!

"Come on ladies, I think you've caught up to me now, right? Let's try out some more of those toys."

I picked out the butt plug next and grabbed a bottle of lube from the bedroom.

The two women got up languidly from the floor and stretched in the sunlight, once more reminding me of cats. Monica helped Kelly onto her hands and knees and gave her a quick kiss before settling beside me to watch. I decided to start off by trying to get her tight little hole relaxed some, so I got behind her and started playing with her bottom a little, licking and kissing her butt cheeks and her crack as I had done the very first time we were together. I spread her cheeks and tasted her sweet juices where they had flowed into her crack. Wetting her pink, clean anus with my tongue, I began to finger it just a little, not really inserting my finger, but exploring and putting a bit of pressure on it just to get her used to the feeling. Her squirming and moaning told me she was enjoying things so far. At last she relaxed enough so I was able to slip the tip of my tongue past the tight knot of her anus, and she let out a deep sigh of satisfaction. After a few minutes of tonguing her ass, I was ready to burst -- my aching cock was dying to be swallowed by that tight little sphincter, but I wanted to make this hurt as little as possible for her.

"OK, Kelly, are you ready to try the butt plug? I'll go slow."

She looked back over her shoulder at me, chewing lightly on her bottom lip, and nodded with a smile that I thought was a little frightened. Monica reached out and petted her lower back, comforting her gently.

I lubed up the plug and began teasing her ass with it, probing just a little bit and circling it around the rim in tiny circles. At last I slid about an inch or so inside her, and she let out a loud moan.

"Feel good?" I asked her.

"Yeah, but it hurts a little, too. Go slow," she answered in a breathy voice.

I was worried that it hurt already, because I hadn't put the plug in very far at all. It was at a section that was maybe as big around as my thumb, and she had a long way to go before she had the whole buttplug in, much less my cock. I looked at Monica, and she seemed to know what I was thinking, because she started to kiss and caress Kelly in order to distract and relax her.

I kept working the plug in deeper just a little at a time, then backing off to a comfortable level. Doing this, we got to within maybe a half inch of the widest part of the plug, but by this time Kelly was calling out and even crying a little. I really didn't want to hurt her, but I have to admit that my cock was throbbing along with my pounding heart at the sight.

"Oh, Mr. Mac! I don't know if I can do this!" Kelly cried after I had plunged the buttplug deeper yet, nearly getting to the widest section. "What if I can't take it?!"

I could tell she was starting to get distressed now, in addition to dealing with the pain, and I knew that would only make it hurt more because her muscles would be tight. I stopped trying to get the plug in any deeper and instead just played lightly with the tip against her anus.

"I have an idea," said Monica suddenly. "Let's try something else!" And she got up to grab the strap-on, which I had almost forgotten.

She put on the strap-on and stood in front of Kelly, with her "penis" in front of Kelly's face.

"Why don't you give me one of those amazing blowjobs Tony has told me about and forget all about him back there?"

Kelly obliged, and soon the slender dong of the strap-on was disappearing into her mouth. I think Monica really liked the stimulation of being in the dominant position, because the pleasure on her face looked totally real, as if she could feel the sensation of having her "cock" sucked. As happened with the double-ended dildo, she seemed to tap into an inner dom that she doesn't usually exhibit, and soon she was fucking Kelly's face hard! I was surprised and incredibly turned on by the sight of my wife thrusting the dong into our young neighbor's mouth completely up to her pubis. She liked to go fast, too, until Kelly would start to retch a little bit, and then she would slow down and let her catch her breath.

I took advantage of Kelly's distraction, just as Monica had planned, and started exploring further with the butt plug. I still went slowly, gradually working it in, but it was getting deeper than it had before, and I thought we would be able to get it fully inserted. I had been having doubts until Monica's bright idea!

I could tell it was still hurting, because Kelly moaned and whined in response to some of the deeper thrusts. I could hardly believe how huge the plug looked entering her tiny body. Finally, during a particularly energetic flurry of throat fucking from Monica, I slipped the buttplug fully home. As it passed her anus, the strong sphincter snapped tight in the groove at the base of the plug, gripping it tightly so that only the flange protruded. I thought we were home free.

"Take it out! Oh god, it hurts, take it out, Mr. Mac!" Kelly had jerked her face away from the strap-on and there were tears streaming down her cheeks, partly from the intensity of Monica's adventures with the strap-on, but partly from the pain, too. "Oh shit, I don't think I can do this!!"

I felt horribly upset and surprised, obviously because she was in pain, but also because she had cursed! In all our talks I had never heard her curse in anger, and I think it drove home just how distressed and in pain she was. The shock rattled my brain and I couldn't think what to do right away, and Kelly was looking at me, her eyes pleading for me to take the plug out. She practically vibrated with discomfort and agitation.

"OK, all right, I'll take it out!" I blurted.

"No, wait a minute." Monica's calm voice surprised me. She stroked her hand down Kelly's back and caressed her hair. "Breathe deep, sweetheart. Your muscles are spasming, but they'll stop. Just relax, breathe, the worst is over, breathe..." Her voice was like a mantra that seemed to penetrate Kelly's discomposure and started to calm her down.

"It'll be better if you can leave it in, honey. Your body will get used to it. Just relax and breathe," I said, matching Monica's hypnotic, soothing tone. For the first time in a while I felt the conflicting influence of parental protectiveness and lover's desire. I wanted her to be OK, not to hurt, but I was also REALLY turned on and really wanted her more than ever. The result was a sensation of almost incestuous shame, but it didn't even begin to tame the fire burning in my heart and throbbing in my cock.

After a time of quiet, calming, murmuring and comforting touch from both of us, Kelly began to breathe more normally and her tears dried on her face. Soon enough, she seemed recovered enough for me to ask if she wanted to continue. Now that the pain wasn't so excruciating, she seemed willing and even a little excited to keep going.

"Yes, Mr. Mac, let's keep going. I really want to do this, and it would be dumb to stop after getting this far."

My heart charged with a new flood of adrenaline, spurred by her words. It looked like this was going to happen after all!

I managed to get the buttplug back out, which was a bit of a challenge because her strong anal sphincter had gripped onto it tightly, and because it caused a new wave of spasming and pain, but it didn't seem to be nearly as bad nor last as long as before. In fact, I spent a few minutes working it in and out past the thickest part, to get her ready to accept my cock.

Finally, the moment of truth. I laid the buttplug aside, and Kelly moved to the couch. She leaned back against the cushions, slouching low and leaning her head back, looking up at me expectantly. Monica sat beside her for moral support (and later, to play with her nipples and clit!). I lubed up my shaft really well and moved between her legs, lifting them and getting her into position so the angle was just right. She was so light I could move her like a doll. I placed the head of my cock against her tight little hole and started to apply pressure. Kelly gasped out loud as the head of my penis slipped past the tight balloon knot of her anus, and I stayed right there for a moment to let her get used to the feeling.

"Doing OK?" I asked, trying to read the expression on her face. Pain and pleasure can look so alike, and sometimes are mingled inextricably together.

"Yeah," she said in a raspy whisper, "but go slow. It really hurts, Mr. Mac." She gave me a tight smile. "It feels good, though, too. Really good. Don't stop."

I gradually slid my throbbing cock deeper into Kelly's tight bottom, carefully watching her face and gauging her reaction. After each advance, I stayed still for a moment and then gradually pulled back out a fraction, making a very slow and careful back-and-forth motion. In this way I was able to get at least 2/3 of my length inside her. At that point, though, I began to feel some resistance and Kelly said she was feeling an odd pressure and pain deep inside. I knew right away what she was experiencing -- Kelly was so small I was coming up against the curve where the rectum turns into the colon. I told her what was happening, and reminded her to breathe and relax.

Monica knew exactly what Kelly was feeling, too, and began to kiss her and suckle her nipples. She even began to rub her clitoris. The combination of pleasurable stimulus, excitement, and desire worked wonders, and soon I had my cock all the way inside her. I have to say, it felt amazing. I could feel each tight muscle, each curve and fold, every sensation amplified by the circumstances and by the slow deliberate movements I was making to ensure Kelly's comfort. Once I got my full length inserted up her ass, I began to slowly stroke back and forth. At first I only moved a few inches in and out, but I worked slowly up to the point where I was gently sliding my full length in and out of her tight asshole. I think the most incredible feeling was when I had drawn almost my entire length out of her, and the tight muscle of her anus gripped the sensitive ridge just below the head of my cock. I loved holding my cock right there and almost, just almost, pulling out, but always keeping the head just inside. She moaned and smiled when I did that, so I think it must have felt pretty amazing to her, too. When I would slide it back into her, I could actually see my shaft moving the smooth flat skin of her lower belly, distending her abdomen just a little, like a baby kicking in it's mother's womb. I couldn't believe how deep inside her I was penetrating -- it was truly mind-blowing!