02 Surrendering to Pleasure

This is part 2 of a fantasy of mine. All the characters are in their 30s

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Continued from part 1...

She pulled back and spread some lube over my ass with her fingers which she very quickly escalated from a surface task to an interior task, not hesitating to slide her digit inside of me and feel her way around. Soon she was fucking me with her finger and I was moaning, slightly pushing my hips back and enjoying the sensation of surrendering to her touch, knowing that for the rest of the night I was going to be doing everything I could to accommodate any desire she wanted to explore with my body... luxuriating in the feeling that she wanted me and wanted my body and found my body to be a source of pleasure in a way that had more to do with what she could do to me and what I wanted to let her have access to rather than what I could do to her (although she was certainly giving me access to a set of desires that were as elusive for her as this was for me). It was the feeling I had been trying to capture for some time and I would learn soon that to be feeling that so early on was a sign that the rest of the night would lead me to spaces of pure ecstacy and wanton lustful disregard for any sense of what was proper or respectable.

The next thing I felt was the warmth from her body inching closer to me followed by her hands on my hips and the large heavy phallus pressed against me. I was nervous about whether I'd be able to fit it inside me let alone take the whole thing but I remembered having luck with a very hung man when I was younger and took a deep breath in anticipation. She asked me to give her directions and tell her what I needed and wanted as we started and as she used the lubed tip to press against me the first thing my mind jumped to was how good it would feel to have her tease me with it first. So I asked her to drag the tip up and down across my hole which she quickly obliged. The feeling of this heavy, thick cock head dragging up and down along my crack and then crossing over the vulnerable opening of my hole and opening up, for just a moment at a time, the outermost layer of my minimal defenses was toe curlingly seductive and I could feel the heat of my desperate desires overwhelming my fears and concerns.

I was so grateful she was such a kind lover and so concerned with making me comfortable because the threat of this massive dildo, if wielded by someone of another temperament, would have been terrifying. Flirting with that danger gave me butterflies and made me feel like the spoiled brat of my dreams. When I asked her finally to try and penetrate me I helped let her find the right angle but as she started adding pressure it was clear that with enough pressure she could have pushed past my defenses and it would have felt like I was being split in half and I was going to need to start very slowly so I asked her for less pressure but to keep going with the slight gyrations she was making with her hips. I could feel every fiber of every muscle of my hole as they, little by little, started to stretch wider to accommodate the massive cock behind me. As I start making more progress I would pull off of it and then start again and it got easier and easier to slide more and more of the girthy beast inside of me.

She had clearly been enjoying it but it was when I first pulled off of it and then slid back on it a bit that I heard the "oh shit" come out of her mouth under her breath in a moment of clear enthrallment. It was all the encouragement I needed and I asked for more lube and started slowly fucking myself against the tip of her cock as I felt my insides being stretched to their limits. I was overly aware that what felt like an entire arm inside me was only the first inch or so and it was clear when it slid in far enough to get to the end of the hard part. As I pressed back it slid into me with ease for about an inch and a half and then felt like it got to a choke point where my insides could expand enough to accommodate the mass of this dildo but at this point there was no way I wasn't going to be fucked tonight. This beautiful, patient, hungry, horny woman behind me wanted this as bad as I did and I was confident at this point that I could stretch further.

I pulled out, asked for more lube, lined up the head with my now stretched out hole and slid it inside, forcing my muscles to relax as much as possible and just like that it went from an inch to two inches to inch after inch burying itself inside me. I could feel the blood rushing to my cock. I felt all of my resistance and any remaining semblance of "what I should do" fade away almost immediately, replaced with a hunger and desire to be fucked like a slut that was so pure and real it was almost feverishly trancelike. I backed up against her again and she started to push back into me. Before I knew it she was sliding the massive cock in and out of me and my legs felt weak under the intense pleasure. I could feel every millimeter of it as it slid out of me, leaving me feeling incredibly empty inside and then again every millimeter as it slowly filled me back up beyond my limits - making my head spin and forcing gasps and involuntary moans of pleasure from my lips.

I was losing myself in the pleasure of the sensations, feeling completely at her mercy and completely surrendered to the pleasure I was experiencing as she used me. Then I heard the familiar panting and quickened breath from behind me that I had heard in the past when she was close. I was overwhelmed by the realization that she was orgasming from fucking me. While I had been lost in the pleasure she was giving me with the strapon she was wearing, she had been enjoying it so much that she had started to cum. I only had a moment to process that realization before I felt her start to spasm and drive the long shaft further into me than I thought was possible. I shuddered and felt my whole body flush with desire as my legs curled up behind me and I pushed back against her, riding out her pleasure driven spasms in a state of unmatched satisfaction. I had only ever fantasized that someone like her could exist and never believed it was more than a fantasy. A beautiful, hungry woman who wanted permission to use my body in this way who was so into it she could cum from it. I had brainstormed solutions for years on how to make the experience as pleasureful for the partner wearing the strapon and here I was having used none of them, with this tall, exhilarating woman cumming with all her might from just the pleasure she got from the act of penetrating me and seeing me not just submit but welcome and beg for the pleasure she had not been allowed to give to such a willing participant before.

My breathing sped up, my moans were strained, the large phallus was digging almost too deep to bear and I just wanted more. I was in a daze of pleasure and my lower legs had curled up behind me, wrapping around the backs of her legs, feeling her soft skin under my feet and using the very small amount of leverage it afforded me to encourage her by squeezing her toward me. After the quaking of her body slowed down I realized she had thrust into me so hard my head was hanging off the edge of the bed and my entire body felt flush. It was after a moment of the two of us laying, somewhat exhausted, with her on top of and deep inside of me that she said, "are you ready?" and slowly withdrew the member from inside of me leaving my hole slightly quivering and feeling disappointingly empty. There was no way I could get up immediately and I told her while I was half hanging off the bed that she could touch me and see how stretched and worn out she had gotten me. She seemed excited to feel it and I felt her fingers exploring my stretched out hole. I assumed that was probably the end of the pegging for the night and when she stopped fingering me I turned to sit in front of her sexy body on the bed. I kissed her and she made a comment about how much fun it was. I agreed and whispered "You did great daddy" with a smirk across my face knowing this would elicit a reaction.

Well... a reaction I got. She laughed and pushed me down onto the bed chastising me for saving the "daddy" for afterwards saying she was ready to go again and asking if I could handle more. Little did she know there was nothing I wanted more than to feel her inside me stretching me out again. She pulled out the panty vibrator I had brought as a surprise for her and I helped her slide it into the front pocket of the harness and turn it on. She seemed immediately on the verge of another orgasm and this time she pushed me on my back and we struggled for a brief moment while we fit the wedge under me - desperate to feel her inside me again, I shuffled around, as best I could and as soon as the wedge was under me I lifted my legs up and exposed my still stretched hole for her. She climbed closer, holding a leg with one hand and the dildo with her other one, taking aim and sliding the head around trying to find that bullseye she could slide into. When she found it, she slowly slid deeper and deeper into me until she got to the base. Looking up at her this time, being slightly inverted on the wedge and feeling how much leverage she had in this position made me feel crazy. I couldn't believe this was real life and not just a dream. Before I could follow that thought too far though, she looked me in the face, her eyes slightly intense and hungry looking, and with an eager smile she asked if she could go faster. There was no hesitation in my response - I wanted it - I wanted her - I wanted my hole to be ruined by the end of this night and I was about to get it. She started fucking me harder, pulling almost all the way out and then slamming back in again, letting me feel the full length of her stroke and slowly switching from a space that felt like it was about me to a space that felt like it was for her pleasure exclusively. As she sped up I couldn't help but encourage her - "yes please fuck me, fuck me harder, yes daddy fuck me" and the reaction I was getting from her was nothing short of intoxicating. As she started to convulsed and her breathing got less steady I wrapped my legs around her, dragged my hands on her back, pulled her into me and as she got close to peaking, as I felt her huge hard dildo slamming in and out of me I couldn't help but say "Yes, please cum! Cum inside of me!" I don't know why it felt right in the moment but it worked for her too and while I was grasping at her and squeezing her into me and begged her to cum in me with her big dick she started to climax, thrusting harder, losing just a bit of the restraint she had shown all night and fucking me into a state of complete ecstatic surrender.

She orgasmed for so long and it was pure bliss. I had thought the first intense orgasm from behind me was as hot as it could get but I was wrong. This was everything I had hoped for and as she thrust into me to the base over and over again I couldn't imagine anywhere else I would rather be. eventually her orgasm got so intense and had gone on for so long that she started to beg me to reach down and turn the vibrator off so she could stop long enough to breath.

I obliged, reaching down while the dildo was still deep inside me to try and hit the button so she could get some relief. When she gained her composure she drew back and slid the huge cock out of me, leaving me feeling the air on the inside of my now ruined hole. It was perfection and that memory will live rent free in my head forever.