Third Time's a Charm! (mf) | 2016

So, first of all - big news, everyone! The girlfriend mentioned in the last couple stories has accepted both my marriage proposal and accompanying sparkly piece of jewelry so she's now my fiancee!

This is a recollection of a particularly hot encounter - that started with a pretty routine evening - that we had somewhat recently. It's quite lengthy, and features oral and anal action. Per usual, little details have been changed here and there to protect identities. But anyway, on with the tale.

After watching the end of a hockey game at the local watering hole, then taking a sunset walk around our neighborhood, we headed back to her place for a cool-off shower and got into bed to snuggle - even though it was still early. I appreciate the fact that she no longer wears clothes for these snuggling sessions, as I love the feel of the full length of her naked body pressed up against mine. She gets really comfortable in these sorts of situations and has fallen asleep in my arms a few times - apparently I make a really good big spoon! After talking for a few minutes, she mentioned that she wanted to show me a few ideas on the tablet, but was far too comfy to make any move toward it. We talked a little more and our conversation slowed, and she started to drift toward sleep. Well, after 15 minutes or so more, my arm is finally getting tired, so I move a little to try to reclaim it, and she snaps awake. I turn on my back and she goes to retrieve the tablet to go over some wedding ideas. After she shows me the ideas, she puts the tablet away and comes back to snuggle, this time with her facing me, and I'm on my back, half covered by a sheet.

After a little bit, she starts to play with my nipples, tracing slowly with the pads of her fingers against my skin, sometimes raising up to drag her nails across my skin, just to vary the experience, I'm sure. I'm almost immediately at full attention, willing her to drop lower to my straining member. As if she could hear my direction, her hand starts to head south from my chest, dancing across my stomach but stopping at my waist to head around to my sides. She then looped her hand back up to my chest and re-traced her steps, dragging her fingers down my chest, over my stomach and turning toward the other side. I could feel my dick pulse with anticipation, and could see the sheet move as it did. She wasn't even looking down, just watching my face as her fingers performed their sexy dance. She asked if I'd like to get the oil out and I motioned with my eyes down to the obvious tent in the sheet... she followed my gaze and said "oh, I'll take that as a yes!" My dick pulsed under her gaze, as she continued playing with my skin a little more, before heading below the sheet to tickle my shaft and balls a little. My dick pulsed again as she wrapped her whole hand lightly around it, stroking it slowly under the sheet. I just lay back and let her work, closing my eyes and enjoying the sensation. After a few pumps, she stopped and her hand emerged from under the sheet, playing once more with my nipples - first right, then left - and she said in a more firm tone, "Oil!"

She busied herself with putting a towel down and I retrieved our massage oil. She laid on her back and spread her legs as I dripped a little oil first on my hands, then on her body. Over her lovely round boobs - with those perfectly set, dark pink nipples perched atop them - around the sensitive skin at the underside of her boobs, and down her sides, over her freshly shaved long tanned and toned legs, then back up to her inner thighs, a little to the bikini area and a little on her stomach. I set the bottle down and started to work the oil into her skin from beside the bed, being rewarded with skin that first glistened brightly in the light - oily slick and crying out for my hands to glide over every inch - then, as the oil was absorbed by the skin, a more muted glow, softened by the additional moisture and massage. Finally, after working in the oil to every other part, I dipped my hand down and brushed past her glistening pussy and partially hooded clit. As I made contact with her clit, she drew in her breath sharply, and my still hard cock pulsed again, causing a little precum to start dripping down. She noticed this and caught it "You're dripping, fiance!"

She used her hand to catch the drip and rubbed it onto her leg. I got a little bit more massaging in on her fabulous rack before suddenly jumping onto the end of the bed between her silky thighs.

She giggled as I practically dove face first into her pussy, lapping at her soft, warm folds before coming up to work over her clit. I paused to get some air and lick my right index finger before burying it inside her. She was so wet I knew immediately she was going to need two. I decided that since I already had some oil going, and she seemed very turned on, that I'd go for some anal play tonight, so I pulled out my index finger, dragged it down past her pussy and paused briefly at the entrance to her backdoor before leaning forward and attacking her clit while I slowly brought my right hand forward, feeling her tighten up around my finger as I buried it into her ass. I licked at her clit for a bit longer before I applied some pressure up from my finger, pushing toward her G-spot from inside her ass. I dropped the pressure and licked at her clit some more, pausing to suck it into my mouth as I pulled my finger from her ass. I smiled up at her, telling her how sexy she was, before re-adjusting how I was laying to bring my left hand into play, this time licking two fingers and inserting them into her wet pussy. She let out an appreciative moan as I pumped them in and out a couple times before pulling them out slowly, and dragging them to her ass. I once again started to lick her clit as I pushed both fingers into her ass, feeling almost as if her ass was going to somehow reform them into a single finger. She dropped her hands to her pussy and pulled her lips apart, exposing her swollen clit to me and I slowed my pace considerably, pulsing the fingers in her ass upwards toward her pussy every few licks to her clit. I felt like she was getting pretty close, but I really wanted her to cum while something a little larger was in her ass than my fingers... so I pulled them out and continued sucking on her clit for a little more before sitting up and grabbing for the oil, dripping some on my hands to spread on my cock. Her eyes widened as she realized what I intended to do.

"Oh really?" She asked.

"If you're up for it" I responded

She grabbed her legs and brought them up to her chest - answering that question - as I sunk down on my knees, lining up my straining cock with her backdoor. "OK" she said, and I pushed forward, feeling an incredible grip from her ass on my cock. She grimaced a little and I stopped, holding it there. I brought my middle two fingers from my right hand up to attempt to play with her clit some, but she waved them off... "concentrate on you!" I pushed in a little deeper and held it there, warning her my dick was about to pulse. (When it's being squeezed hard, I feel like I have a little more warning than normal... and she appreciates the warning, especially in the early stages of insertion.) She seemed to steel herself, but when it pulsed, she gasped and pushed me away, taking a couple ragged breaths before suggesting that maybe we could try a different position. Obviously, I was game for a new position, and she turned over, presenting her beautiful round ass in the air right in front of my dick, while on her knees, back arched, and chest low against the bed. I grabbed more oil and spread some between her cheeks and over her tight little hole, then spread more on my still rock hard cock. I got my hips up behind her and lined up to try again, this time asking her to push back against me. She pushed back a little, but then asked me to push in further. I followed instructions and once again was greeted by an ultra-tight grip on my shaft. I paused and walked my hands over her back, giving a light massage to try to relax her a little, then once again felt that pulse welling up in me. I warned her and she simply said "OK." My dick pulsed and she gasped at quickly pulled away... "you're just so wide!!"

I reached down and rubbed her pussy with my middle fingers on my right hand again, before she stopped me and flipped over, looking up at me from her bed. "What do you want?"

I thought about it briefly and replied "I want you to cum!"

"I want you to cum, too." She replied.

I moved between her legs and began licking her clit again for a little bit before she asked me to go wash up. "I want your fingers inside me."

I washed up at the sink and returned, licking my two right hand fingers and inserted them into her waiting pussy. She sighed relief as I buried them to the third knuckle, probing her deeply as I set about to make her cum. I curled my fingers up to hit her g-spot and could feel the mouth of her vagina pulse around my fingers with each lick against her clit. She reached down and pulled her lips apart, and I paused briefly to take in the view, fingers still buried deep inside her womanhood, her clit nearly as big as I've ever seen it, begging for attention. I brought my index finger up from my left hand, put it atop my two right hand fingers, and slowly pushed it forward, earning a deep moan from my fiancee. I resumed licking her as I pulsed the right fingers, then the left finger upward every two licks to her clit. After a little bit of this, I pulled out my left finger and dropped it to her ass, pushing it in all the way as I picked up the pace on her clit, now licking almost as fast as I could, I couldn't keep up pulsing my fingers with every 2 licks so now it's every 4, first curling my right fingers to massage that g-spot, then curling the left to feel the right fingers through her walls. She started to moan loudly now, "don't stop, don't stop!" I could feel her ass pulse first as the first wave of orgasm hit her... her pussy tightened hard around my fingers shortly after, as she let out a loud cry. I popped the left finger out of her ass and continued to lick her clit and rub against her G-spot, in a slower fashion as her orgasm crashed over her body, causing her thighs to squeeze together briefly every couple seconds. I curled my fingers up in her pussy and she shot forward in the bed, before crashing back down on the pillows and pushing my head away. I held my fingers inside her, waiting for her to come down while occasionally pulsing them upward until she pushed them away, too.

She smiled at me and I bounced out of bed to go wash my hands, then re-joined her and laid on top of her and kissed her some. I held her for a little bit then she asked that magical question... "do you want to try one more time?"

"Third Time's a Charm!" I replied... and I suggested we try on our sides this time.

I lubed up my cock and she lubed up her ass some more, then I moved behind her and pushed my cock in between those lovely cheeks. She adjusted her hips a little and I could feel a little heat from her ass, just asking me to push further in, I'm sure. I pushed my hips further and could feel her tight ass give way and allow my thick member entrance into the darkened tunnel. I pulled her hip toward me then held her, to try and let her ass adjust to my width. I could feel another pulse welling up and warned her. She let out a little moan when it happened this time, then shortly after, pushed her hips back off my cock. I held her and started to slip my dick between her cheeks, just liking the feel of her oil-slicked skin against my cock. I mentioned how sexy she felt as I drove my hips forward a little, feeling the tip open her up a little before reversing course and backing away. I applied some short strokes, rubbing my dick up against the hole before again, just getting the tip in before getting back out. After a couple more tries of that (and subsequent exclamations of how incredible it felt), she started to back her ass up into me, causing my short thrusts at her entrance to penetrate more than just the tip. I started to thrust my hips forward a little more and soon the head was disappearing into that incredible grip of her anal canal. "I'm going to try going deep" I warned her. She reached back and pulled my ass toward her (God, what a woman!), I pulled her hip to min and rotated my hips to get as deep as I could inside her with an emphatic grunt from me as she moaned. I warned her that my dick was going to pulse and she gasped as the pulse came moments later, I pulled completely back out and once again used shallow thrusts to again work my way back in, a few thrusts and then just the tip, a few more thrusts culminating in the head popping past her tight sphincter, and after a couple thrusts stimulating right where the head meets the shaft, I warned her again that I was going to go deep, and again pulled her hip toward me as I rotated my hips forward for the full length. This time, I could feel her back her ass up in an effort to get me deeper still! (God, what a woman!!) I could feel my orgasm building as I performed quick little thrusts now, moving my hips in and out to bury the full length of me in her well lubricated ass over and over again.

I abruptly changed tactics and pulled completely out of her again, then, slowly re-introduced the head into her waiting ass, before reversing course and starting over again. I couldn't contain myself at that pace for long, however, as I could feel my orgasm growing stronger still. I wanted to fill her little ass with cum, and my pace increased again, feeling her ass stretch out every time my dick slid in and out. I was thrusting about half way in, then heading all the way back out just to feel that marvelous stretching sensation over the most sensitive part of my dick once again. I warned her I was about to cum, and she encouraged me to cum inside her... I couldn't last any longer, so I pulled back hard on her hip and drove hard into her, and my dick started spurting my warm cum deep inside her, while she moaned her delight.

It felt like one of my biggest loads ever, and I whispered in her ear how sexy she was, as I could feel her ass pulsing around my now softening dick. I nibbled on her earlobe and held her there, sweaty and spent, dick still half buried inside her. After a few heavenly minutes of basking in post-orgasmic bliss, along with the usual "I love yous" that follow excellent orgasms, we got up and rinsed off before returning to bed and resuming the position that started it all... Me as the big spoon and she nestled against my body in my arms. This time, however, we fell right asleep. My last coherent thought of the night? "God, what a woman!!"

Thanks for reading, and I hope you enjoyed it nearly as much as I did!

To my fiancee: thanks for being so amazing, and I can't wait to marry you!! Every day feel like a special occasion with you!