Lowering her eyes, lowering her head, she said,
"Please, sir, may I ride your cock?"
I had been looking forward to fucking her but the thought of the woman of my dreams sitting on my cock while she fucked me wasn't something I was going to say no to.
I lay back and, without even a moment's hesitation, she pulled herself up and straddled me. Still not looking me in the eye, she grabbed my aching cock and directed it towards her pussy hole. She was obviously still nervous and more than a little afraid so she rubbed the head along her slit but we both knew she didn't need any more lubrication. Her pussy was literally dripping and I wondered how tight she might be. She was older than anyone I had ever fucked and she had two adult daughters so I wasn't expecting much in that sense but she still seemed to be squirming as I entered her.
As it seemed to take a few attempts for her to get me all the way in, I began to wonder if my cock was bigger or thicker than what she was used to but I then remembered that she had told me how long it had been since her husband had even looked at her, never mind fucked her, so I lay there and waited.
I watched as she bit her bottom lip with the effort before she finally slid all the way down my cock and let out a sigh of relief and contentment. The moment she did, however, she started to ride me, slowly at first, as she and her pussy were obviously taking their time to get used to being filled once again. She soon speeded up though and she wasn't the only one moaning in pleasure as I reached up and played with this gorgeous older woman's luscious breasts.
As I played with and pulled on her nipples it became obvious she wasn't going to last long even though it wasn't so long since her last orgasm. She leaned forward, her hands on my own chest and began to fuck me hard, very hard, sliding up and down my cock more and more urgently. I wanted to make this a day for her to remember, a fuck to remember, so I pushed up too, rising to meet every one of her downward thrusts. I could feel my own orgasm beginning to build too, my balls tingling, ready to erupt. As she became almost frenzied in her riding, her whole body lost in the moment, sweat covering her skin, she suddenly stooped, silent, and her whole body seemed to shake. I continued to push up into her, watching in delight as she came again and again, the walls of her pussy squeezing my fat cock before she collapsed on top of me.
As she slowly came down from such a high, I somehow managed to slide out of her, my still stiff cock making an obscenely pleasant sound as it pulled out of her satisfied pussy, and rolled her over to the other side of the bed. We both knew what was to come next and, whether she was conscious of doing it or not, she conveniently rolled on to her front.
I got up from the bed and retrieved the oil from the bedside table. My older lover had one more bridge to cross, one more hole to surrender, and I wanted her to enjoy it as much as she had obviously enjoyed the rest of her day. But to do so she would have to try and relax even more and that's where I hoped the oil would help.
Having poured some of it on to my hands, I placed them on her upper back, starting with a smooth gliding motion, spreading the massage oil across her back and shoulders in broad circles. I'd done this before, many times, and I kept the pressure firm but comfortable as I concentrated my efforts far away from where we both knew I was headed. To take her mind off what was coming, I moved up rather than down and gave her neck a long, slow rub before deciding to make my move.
Sliding my oily hands down her sides, I gently brushed past the sides of her breasts. She probably hadn't been aware that they had pushed out slightly because she was lying face down and her body trembled at my slight touch. She didn't seem to mind, though, and certainly didn't object so I continued my downward journey, down over her lower back, before I decided I needed more oil.
Still determined to take my time, even though my cock was straining for release, I moved down to her legs and, starting on the right, lifted it back at the knee to massage her calf and ankle. I lay her leg down before doing the same on the other side, only this time sliding up to her thigh. I could feel her tensing here again so I moved back to her right leg and covered the back of her other thigh before moving on.
I wiped my hands on a towel I had lying by the bed and leaned forward to whisper in her ear.
"It's time."
She shivered as I knew she would but once again she proved that she could still surprise me. Reaching back with both of her hands, Sally grasped both of her round cheeks and spread them fully open. I think my jaw dropped looking down at this incredible older woman lying in front of me spreading her cheeks and showing me her forbidden hole.
We had spoken about this but I still couldn't believe it.
"Are you sure, Sally?"
"Please, sir, just do it. I want you to take every inch of my body."
"Your wish is my command, you little slut. Prepare to take my cock up your dirtiest hole and know that I am going to cum deep into your bowels like a cheap whore."
She trembled once more, in anticipation and in the realisation that my filthy words were exactly what she wanted to hear. But if she could surprise me then I could surprise her too and I leaned forward to plant a long wet kiss right on her tightest hole. She whimpered this time but not for an instant did she relax her grip on her backside. I wondered for a moment what she would do if I licked her there too but my cock wouldn't wait any longer and I reached for the oil one last time and thoroughly coated the head of my cock with it. I knew I would have to apply some to Sally's hole and so did she but she still flinched a bit at the feel of it. Taking my time, I lightly worked the oil into the crevices and ripples of her tight hole, again enjoying the feel of it, as well as the feeling of power as she squirmed beneath my hand.
I thought that Sally had done surprising me but the more I rubbed between her cheeks, and the more she got used to it, the more she seemed to relax and even began to respond by moving her bottom in tight little circles, trying to hide her moans of appreciation by burying her head in the pillows. Time to move on.
I gently pushed my oil-covered finger inside, meeting no resistance other than a delightfully tight hole. I could feel her backside gripping my finger as she raised her bottom off the bed, apparently hungry for more. This went on for a few moments while I made sure that she was thoroughly lubricated and making sure we were both enjoying every sensual moment. I withdrew my finger and once more whispered in her ear.
"You're ready now, my little slut," I told her as I pulled her up by the hips, just enough to allow me to pull a pillow down and push it.
She took a deep breath and seemed to hold it but I told her to relax and to breathe normally; this would go as fast or as slow as she wanted. After what seemed like an eternity, I placed the round head of my cock at her tightest entrance and wondered as I always did how such a large thing could enter such a small hole. But enter her I did as I leaned forward and took away her final virginity. The thought that a woman of forty seven still had a virginity to give was as amazing to me as it was to Sally herself.
Again she buried her head in the pillows, as she only now seemed to realise that my cock was going to be much larger than my finger. I could feel her forcing herself to relax but it still wasn't easy to get it in. Taking my time, however, I pushed in just a bit, then paused, then pushed in again a little harder, a little deeper, before pulling back. I had to allow her to get used to this strange, wonderful sensation, just as I was doing with this amazing woman.
When I finally made it all the way in, she asked me to stop for a moment which was fine by me as it gave me the time savour the moment and the sight of her most private hole stretched around my cock. It felt so nice, so very nice, and I stayed still for a moment longer to enjoy it.
I could hear her breathing being measured and controlled as she fought the natural reaction to pull away. But I knew she also wanted to relax; I knew she also wanted to do this, to strip away the last of her fears, of her inhibitions.
I slowly began to push in farther, then out again, each time going in a bit deeper. She was incredibly tight but that just made the feel of her tight ring rubbing and massaging the head of my cock as it worked its way in and out of her gorgeous arse all the more enjoyable. Finally she began to meet my forward movements with her own pushes back. Whether she was aware of it or not, she even wiggled her backside from side to side, making the whole experience even more awesome, both physically and visually. She now seemed to be fully welcoming my hard cock as it moved in and out of her arse, no longer resisting me.
I reached under her and began to stroke her soaking wet pussy. She was obviously enjoying what we were doing as much as I was and she turned her head and smiled at me as my fingers lightly touched her sensitive clit. At the same time I began to rhythmically move in and out of her darkest hole, never pulling out too far or moving in too deep, continuing to play with her cunt as she continued to drip with arousal. I pumped my cock in and out, getting faster now, my fingers moving in time with my cock, her pussy being treated just as well as her arse and my cock.
"So good," she whispered, almost to herself. "It feels so good." And I'm sure she was wondering why she had waited so long to feel this way; I know I was. As I began to really plough in and out of her, she pushed back even more, both of us lost in the animalistic fucking that we were enjoying so much.
As my thrusts became too fast for her she simply lay still, and let me fuck her little beautiful hole, giving herself to me as she had never given herself to any man, not even her husband. Faster and faster I plunged into her, deeper and deeper, lost in the most wonderful sensation, lost in my lust for this wonderful woman.