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She started to slide the toy up and down the valley between my ass cheeks
#1
We had met in an Internet chat room. Nothing special for a lot of people out there, but I'm in my fifties and this was all very new to me. It was strange being able to talk so frankly with someone I had never met face to face. In fact it was so open that I found myself sharing things that I had never spoken about with anyone. It was such a freeing experience, yet frustrating at the same time.

We maintained fairly regular private chats and got to know each Other’s desires. Sharing fantasies and sex in cyber space. That some of our sexual bents coincided made things even better. I had confessed my desire to wear women's panties while making love, and she, the exhilaration that came from thinking about a sexual encounter with a man wearing women's clothes.

Once, I wore a pair of thong panties while we were chatting. This was my first experience with cyber sex. The newness of stroking myself while reading each line she would deliver to me describing what she was doing to me. The pace, slow and deliberate. Allowing my mind the time to savor each step in our virtual lovemaking. The excitement I felt waiting for the next line to appear in my chat window. The images flowing through my mind, anticipating what she would do to me next.

She had started our encounter in a small, candle lit room. Only a table, supporting the candle, and a futon cushion on the floor. I was lying on my back with legs bent at the knee, feet flat on the mat. She knelt on the mat between my legs. Looking down at me I was suddenly aware I was submitting to her. She had instructed me to wear nothing but a pair of thong panties. Something she knew from our earlier conversation excited me.

As I visualized this in my minds eye, I could feel my erection harden. My breathing began to quicken, anxious as to what might happen. She placed her hands on my knees and began to slowly move them outward, exposing my growing, panty covered, erection to her steady gaze. Her hands left my knees and began to move sensuously along my thighs. Still moving my legs farther, and farther apart. I suddenly felt her fingers tracing the outline of my cock as she grazed the fabric of the panties covering it. A moan escaped my lips as the continued to stroke me through the silky fabric.

Her gaze never moved away from mine. Her half smile promising pleasure, and maybe pain. Her finger then began to trace circles around my cock head. I could tell my pre cum was leaking through the fabric and she was spreading it in ever widening circles. I watched in rapt attention as she slowly raised that finger to her mouth and gently spread the wetness on her lips. She then stuck her tongue out to slowly lick the length of her finger.

Her eyes still locked on mine, she leaned forward, her breasts grazing my thighs as she came closer to my face. She placed her glistening lips against mine, her tongue piercing my lips invitingly to share a wet kiss. I could taste myself on her lips and tongue. During this exchange, my cock involuntarily jerked. Her hand still stroking me, when she felt my reaction, she pulled back from my face. Her smile now full with the pleasure that comes from the recognition of accomplishment.

Once again in a kneeling position, I could feel her hands at my hips, grabbing my thong. She began to pull it up my raised thighs, and over my knees and down to my ankles. For the moment, at least, I was at her mercy, as she had my legs entangled with the panties at my ankles.

Suddenly, she leaned forward again, her face touching me, lying against my cock. Rubbing her cheek against me, spreading the slickness along the side of her face. She turned her head, licking along it's length, pausing to purse her lips over the crown.

Her hands slid to the back of my thighs, her palms pushing my legs up, lifting my feet off the mat. Continuing the push, she soon had my knees on either side of my head. I felt more exposed than I ever had before. She leaned forward again, and began to swab my balls with her wet tongue. Then, reaching lower, her tongue trailed down to my anus. Licking me there, occasionally poking her tongue against the resistance of my sphincter. I could feel the wetness she left there. My anticipation grew with each excited breath I took. I wondered what she would do next. I feared, and hoped, that her attention would continue to focus on where she was right then. Just then, I felt something else lying against my ass. It wasn't flesh, but was still somewhat soft. She continued to look right into my eyes. I felt the new object leave my flesh. I saw her bring her hand up toward her face. In it was a small dildo. It was only a few inches long, and not much bigger around than my thumb.

She lifted the phallic symbol up to her lips, and slid it into her mouth. Her eyes searched mine for acceptance of what was about to happen. My mind was whirling now. I had fantasized about a woman making love to me. Dreamed about a woman putting on a strap-on rubber cock, and making love to me as a man would make anal love to a woman.

My hand had moved down to grip my cock. The amount of pre cum on my belly provided more than enough lubricant and I slowly began to stroke myself. I continued to watch her move the dildo in and out of her mouth. The questioning in her eyes gave way to excitement and she lowered the dildo back down between my legs. Again, I felt its presence against my skin. She started to slide the toy up and down the valley between my ass cheeks.

She looked down at my cock, my hands still slowly stroking it. She leaned forward again to lick up a drop of pre cum, then pushed her head down, her lips pushing my hands out of the way as she engulfed my cock with her mouth. Then, just as she had all of my cock in her mouth, I felt the dildo start to press against my anus.

The excitement was excruciating. A fantasy about to be realized coupled with the awesome things she was doing to my cock with her mouth and tongue. The dildo began to enter my body. The burning sensation reminding me that this is something I've not experienced before. She kept pushing until I felt her hand against my skin and knew that she had pushed all of it inside me.

She tilted the dildo upward, toward my belly. I felt it rub against my prostate. The feeling was incredible. All of a sudden, I felt very warm, inside. She continued to move in and out, in and out. All the while she was making love to my ass, her mouth was making love to my cock.

I rested my hand on the back of her head. Not pushing her, but stroking her hair as she made love to me. I could feel my orgasm start to build. My hips began to move up and down. She matched my actions, never missing a stroke with the dido or her mouth.

I began to groan as my feelings and thoughts built toward my climax. I could feel it before I heard it. A vibration against my cock as it slid in and out of the warm cavern of her mouth. She'd begun to hum. My hips began to jerk involuntarily. My breathing had gotten labored. She pushed her face against my belly and held my cock deep into her mouth. The imitation cock was being stroked in and out of my body.

I raised my hips high off the mat. My body went rigid and I began to shoot my seed into her mouth. With one hand she pushed the dildo in as far as it would go, and started to twirl it around inside me. She wrapped her other hand around my cock and began to milk any remaining cum into her mouth and she sucked on the head. Those feelings were incredible, indescribable. It was the most intense, most fulfilling climax I can remember ever having.

I felt her toy leave my body. A feeling of emptiness remained. Her head lifted up, my cock slipped from her lips. She leaned forward. This time, covering my body with hers. Her breasts flattened against my chest. Her face lowered to mine as she opened her mouth and covered mine. Our tongues entwined and dueled within our mouths. Moving from mine to hers, and back again.

She moved her head to the side of mine and whispered into my ear, "Next time, my love, I will properly fuck you." I shivered in anticipation.
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