Hottest Jack-and-Jill Experiences

There are scenes from mutual, face-to-face, voyeuristic masturbation that I treasure to this day. I love stroking my cock while kneeling between a woman's legs, where I can see her bare thighs and follow the smooth, soft skin all the way to her exposed pussy. As a horny teenager who had never seen a pussy or even a picture, I would masturbate about seeing those bare thighs leading to a pair of white cotton panties and try to imagine what was underneath the thin fabric that stretched over her crotch. But now I got to see it all--bare thighs, swollen labia and clit, wetness, and best of all, her finger touching it. That sight makes me crazy inside! I love to see her finger circling around her clit. Even more, I love to see two fingers disappear all the way up to her knuckles. The very thought that she is feeling the inside of her cunt while I watch is so intimate and raw. I straddle one of her thighs and feel the warmth of her leg against my balls as I stroke myself. Then I kneel closer her crotch and guide the tip of my penis just inside her hole, wanting the warm fleshy tip and the tease to add to her arousal. I move it slightly as she circles her clit faster and builds up to orgasm. Another favorite position for mutual masturbation is straddling her chest, where I can squeeze her breasts between my thighs and watch her erect nipples push up towards me. It is sexy to look down on my bare dick and her bare breasts at the same time. I watch her face as she looks at me, knowing that she sees my hard dick and knows I am beating off. I am not masturbating all the time, though; mostly just enjoying being in the moment with her. I rub my nipples and take in the whole scene. I drag the shaft of my erect penis over her nipple, from my balls to the arrowhead under the tip, and then circle the tip around her nipple. I lean down and suck my own drop of wetness off of her nipple. I put my hard shaft between her breasts and we both watch in amazement as she or I squeeze her breasts around it. I reach behind me and feel for her pussy. I want to know how wet she is and how hard her clit feels under my fingertip. I find her hand there fingering herself and I am even more turned on. Both of us work on her for awhile, but knowing that she is not going to cum this way. No, not yet. Maybe I will go down and eat her to orgasm. Maybe we will fuck. Or maybe I will lay between her legs with my face close to her pussy as she diddles herself to orgasm, then lick her cum out of her. She is going to have an earth-shattering orgasm tonight, I am sure of it! The woman with whom I had my best jack-and-jill experiences was ten years younger than me and very--even darkly--erotic. The first time we were together I asked hesitantly, "Do you...masturbate?" and she replied easily, "Uh huh. Do you?" From then on I wanted to see her do it, but she didn't seem to pick up on it. One night, after I had eaten and fingered her to orgasm, I said "I want to see you make yourself cum." To my utter delight, she told me which drawer to look in for her vibrator and where to plug it in, and then talked me through how she did it while I knelt between her legs beating off lightly and watching. That was INTIMATE! She explained how the sensations would become too intense, so she would turn off the vibrator and let it rest it on her leg for a few moments, then turn it on again. Her vibrator had a cup attachment and she showed me how she placed the edge of the cup against her clitoris. I would have loved to see her finger herself, but she said the vibrator had made her too lazy. A few days later she recalled the experience, saying "I really WANTED to cum again that night. I really did! It was like somehow you knew. I felt like you are the master of me." I took it to mean that she wanted to masturbate in front of me that night even before I asked. I loved that!! On another occasion, when I was eating her pussy, she said "I need a finger right now!" I knew what she meant but I made her ask for it by saying "Where?" She hesitated and said "In my...ass." I loved hearing her confess that she wanted something in her ass and accommodated her fully, teasing her hole with my fingertip before sliding all the way in. She put her middle finger on her clit and rubbed in circular motions while I slowly rotated my finger in her ass and reamed out her cunt with my tongue. This beautiful, sexy woman was masturbating right in my face! It was thrilling to be that intimate with her! I, too, have often craved a finger in my ass while masturbating or having a blowjob. One of the sexiest moments was straddling over her face and feeling her mouth on my balls and her hot finger up my ass with plenty of Vaseline while I stroked my dick to orgasm. I liked her seeing my hard dick up close and the helpless feeling that I was completely busted, like being caught doing my most private and forbidden things. One night, for her second orgasm, she said "I want to cum again, but this time I want some pain." She wanted me to be rougher with her nipples--twisting, squeezing, pulling. I didn't have the heart that but she was craving it, so I said "Okay, but you have to tell me everything you have ever had up your ass, or thought about having up your ass, while I stimulate you." So she told me about her anal-erotic experiences. There were long pauses when I knew she was totally absorbed in the sensations or thinking of what she would tell me next. It was like a sexual confession and it went on for a long time. I wanted to know things like when was the first time you ever put something in your ass, or thought about it? How old were you and what took you there? I wanted to feel the parity with her of knowing that she thought about and did anal things too. I still masturbate to the memory of her telling me her secrets, and still think of questions I wish I had asked. On our very last night together, staying in a fancy hotel suite, I was standing up and masturbating with my ass pressing against the edge of a high parson's table. She knelt in front of me taking some Vaseline from the jar and then casually reached under my balls, felt for my butt hole and slid her finger in me. She told me later that it really turned her on to feel like she had me pinned up against that table and could do anything she wanted to me. We were quite a match! I never saw her again but a few months later we had a long phone conversation and ended up masturbating together on the phone, reliving our memories. I asked what were your favorite times together" She answered, "Masturbating was the most intimate thing we did together." I agreed!