So I posted the true story of my friend Sally (not her real name) and I over here reddit!. Even though we have never done anything other than what was listed in that story I always fantasize about what might have happened had I A. ever made a move before that night or B. I had stayed later that same night. So here is how I see the second scenario playing out starting after our make out/heavy petting session and her coming back after putting her daughter down.
Sally came back into her room after putting her daughter to bed and laid back down next to me on her bed. We immediately picked up right where we left off. I grabbed her tight and started to kiss her again just as passionately as before. Our tongues wrestled as we made out for a long time both of us just soaking up the moment that had been 7+ years in the making. I pulled off Sally’s shirt and sports bra leaving her perky C-cup breasts exposed for me to see for the very first time. I was completely in awe at how perfect they looked and couldn’t help but let Sally know this. She then took my shirt off and we went back to making out like teenagers again. I kissed up and down Sally’s neck and softly nibbled on her earlobes while I whispered in her ear telling her all the dirty things I was about to do to her. I saw how much this turned Sally on and kissed my way down to her breasts slowly kissing and sucking on one nipple as I played with and pinched her other nipple. I alternated between her breasts while every now and then kissing and sucking on the upper and lower parts as well as slightly nibbling on her nipples. By now Sally was so worked up she was begging me to go lower and I was more than happy to oblige, while I was still working her now super hard nipples with my mouth I slowly slipped my hand into Sally’s pants just enough to tease her clit a little. Sally was soaking wet already as I softly grazed her clit with my finger just enough to make her squirm in pleasure. It was then that Sally started grabbing for the rock hard bulge in my pants but I took her hand away, pinned them up above her head, and whispered to her that she had to wait for that because I was going to pleasure her first. With that, I softly kissed my way down her body to her belt line and slid her pants off revealing her thong which was completely soaked through. I asked Sally if I had made her excited and she told me that teasing her had made her uncontrollably horny and begged me for release. I told her that I wasn’t done yet and slowly put my mouth over her drenched, thong covered pussy and held it there breathing on it for a moment before I softly kissed her inner thigh. I made sure not to even go near her pussy as I kissed and licked up and down her inner thighs and that made Sally beg me to finally pleasure her and I made my way to her pussy. I pushed her thong to the side revealing the most perfectly shaped, freshly waxed pussy that had her juices running down her pink lips. I briefly ran my tongue up and down her pink lips and finally slid her thong off before going back to slowly and softly running my tongue from the bottom of her pussy all the way to the tip of her clit and back down. This made Sally quiver as I slowly teased her beautiful kitty. Then I went for the kill. I spread Sally’s lips open and started to devour her pussy in a way that she had never experienced before. As I alternated between flicking her clit with my tongue and sucking on her clit I begin to insert my finger into her now very lubed up and tight little hole. Sally had to cover her mouth to muffle the screams that were coming from her mouth as I made her cum so hard that it gushed out all over my face. She had her cum dripping down her thighs and all the way down to her sweet little asshole. With my finger still working her post orgasm twitching pussy I pushed her legs up higher and licked her clit and down her lips taking in the wonderful taste of her juices. I just went lower and lower until Sally started moaning and squirming around because my tongue had just found her cum soaked asshole. She didn’t even know what was happening as I licked around cute little hole. She moaned to me that no one had ever done that before and when I stopped to look up her she begged me not to stop. I smiled at Sally and went back to feverishly fingering her and rimming her asshole until I felt her pussy grip my fingers again giving me the signal that she was about to cum again. I maneuvered a bit so I was kneeling beside her now and just concentrated on fingering her little spot until she released again little gushes of her juices spurted out as her body lay twitching on the bed I looked at her, undid my pants and told her it was finally her turn as I whipped out my beyond rock hard cock.
Source: reddit.com/r/eroticliterature/comments/3b7wwt/if_only_i_had_stayed_part_1
I grabbed Sally and started kissing her again so we could both share the amazing taste of her juices. This excited her so much she put a finger inside her and pulled it up for both of us to share and I was already going through withdrawals from eating her out… I NEEDED to taste her again. I tried to go back down on her but this time she was the one pushing me down and told me that she already got hers and now it was time for me to get mine. Sally pushed me over on to my back and in one swift motion had my pants down and fully hard 6.5” cock pulled out. “Damn that was fast” I thought as she stared at it for a moment before she slowly popped it into her mouth. Sally really knew what she was doing as she slowly traced her tongue around the extremely swollen head. As Sally was teasing me I put my hands on her head and played with her luscious long hair putting it into some half-assed pony tail shape. I tried unsuccessfully to make her go deeper but with my dick in her mouth she told me not yet. My cock was twitching as Sally moved her tongue around the tip and slowly sucked on the head. She moved from the head and started to lick up and down the shaft with such precision I swore she had to be a porn star. Just as I was becoming used to the sensation of her slowly licking my entire cock she looked at me, put her sweet lips around my cock and started bobbing up and down ferociously on it. HOLY SHIT was she going fast and hard with about ¾ of my cock in her mouth. The sensation was growing so fast I swore I was about to cum right there. Just the sight of this beautiful woman working my cock in a way I had only dreamed of would have been enough to get me off but tonight was different. Tonight I was hell bent on outlasting her. I took her halfway made pony in my hand and pulled it tight so she was forced to come back off my rod and then slammed her face back down. She took the whole thing in her mouth and was gagging and I repeatedly face fucked her. Each time she would come up she would breath heavily and a large glob of spit and precum would drip from her mouth and then I would slam her face back down again. After a few minutes I knew I would have to stop this or I would explode so with one last push I forced her to take all of me in her mouth and held it there until she came up gasping for air. Luckily this spark of dominance turned Sally on even more and she kissed me hard letting me taste the saltiness of my precum before standing up and lowering her even more soaked pussy onto my face. She told me that I wasn’t the only one who could dominate as she rode my face. Sally grinded her pussy into my face as hard and fast as she could as I lapped at her clit and tongue fucked her hole only letting up for a few seconds so I could catch my breath before she attacked my face again. After about five minutes of this I could feel her body tensing up and I knew she was about to cum again. Spurts of her sweet juices flooded my face and I tried to lick up every last drop of her sweet cum. After she came down from her euphoria Sally went right back to work on my cock and balls. Still in the 69 position Sally was alternating between sucking on my balls while stroking my cock and sucking my cock like it was her job. After a few minutes of this I told Sally that I NEEDED to be inside her right now. Sally hopped off my face and gave me the sexiest look I had ever seen and laid back down on the bed. I got up and looked Sally in her sexy little eyes, kissed her hard and passionately and slowly slid my spit/precum covered cock into her tight little pussy.
Sally let out a long moan of pleasure as I slowly buried my cock inside her tight pussy making sure she felt every inch. I was finally balls deep inside this girl that I had dreamed about for much too long so I just laid there all of me inside her and looked into her eyes and kissed her. After we shared that passionate moment we started to make love. Sally grabbed my back and kissed my neck as I slowly pumped in and out of her. This was definitely the best mix of love, passion, and desire as I held her and she held me. After about ten minutes of us loving each other and taking in the moment that had been way past overdue I pulled out, made eye contact with Sally, and then slammed my cock deep inside her soaked hole. I repeated this pulling all the way out and then as hard as I could went right back in getting deep inside Sally progressively getting faster until I was full on pounding her. Pinning Sally’s arms above her head I pounded her without mercy. Sally bit her lip so she wouldn’t scream as I felt her pussy clamp around my cock as she came but I didn’t let up. As her orgasm was subduing Sally whimpered and told me to lay down on my back. I did as I was told so I pulled out and laid down as Sally mounted me. She slowly lowered herself onto my shaft and pinned my arms down so I couldn’t move and rode me hard. Sally bounced up and down as fast and as hard as she could. I couldn’t believe how hot her controlling attitude was. I was now her toy and she controlled how fast and deep it would go. Sally alternated between riding me like I was the last fuck she would ever have and then slowly so she could control her pleasure. She released her grip on my arms and started rubbing her clit and took advantage of this moment. I grabbed Sally’s ass made her lean in close and using the bed as leverage started to pound her again. Sally buried her face into my shoulder and started screaming as she released the orgasm that was building upside her. Her pussy had a death grip on my cock and I didn’t know how much longer I could last as I was still feverishly pounding away on her pussy. Just when her first orgasm let up a second, much harder one hit her and juices squirted all over my cock. I slowly let up and pushed her off me to position her on her knees. I bent over and started running my tongue all along her pussy and ass so I could once again taste her sweetness. Then I got up and inserted my penis into her from behind taking nice long strokes. Something came over me while I was doing this and I knew that this would be it for me. I pulled her nice long her as I started going harder and faster inside of her beyond pleasured pussy. I was going full force now and decided to smack her ass a few times. With one hand pulling Sally’s hair I took the other hand and smack her perfect butt a little harder each time all while fucking her relentlessly. Sally was full on screaming as her final orgasm was building so I shoved her face into the pillow to muffle the noise a little. I knew I was coming soon because I was still pounding her as hard and fast as I could. With a few last strokes into her I pulled out and positioned us back into missionary for the finale. I grabbed her and kissed her as I slowly started pumping in and out of her pussy. Then with one last hard stroke I came deep inside her. There must have been 7 or 8 long shots as my cock flinched inside Sally filling her up with my seed. I collapsed onto of her and she kissed my ear and neck and told me that she loved me. I just laid there still inside her feeling our juices mix together and had just enough energy to tell her that I loved her too. The rest of the night was spent with us cuddling and kissing because neither of us had the energy to do anything else.