Jack & Jill Party

I had no idea what might come of the ad I placed in the Yahoo personals seeking participants in a jack and jill party for the region I lived in. I was also a little concerned about whether people could indeed restrain themselves and simply keep the meeting to a masturbation activity. For those of you who are not familiar with a jack and jill party, it simply refers to a get together of males and females where the participants masturbate while the others watch. I had never tried it myself but had always been fascinated with the concept. I also felt it was a safe way to experience sexual activity with others. I had once gone to an adult bookstore and there had been some video stalls in the rear of the store. The stalls had 6” holes in the walls to accommodate insertion of penis’ so the person in the adjoining booth could provide a blowjob if they so wished. A male in the adjoining booth had placed his penis through the hole into my stall and I must admit that I did fondle and stroke it but I did not want to suck on it. When he pulled away from the hole he had masturbated as I watched through the hole and it turned me on enough to also masturbate very quickly while he watched. I found the whole experience extremely erotic. This was the motivation behind placing of the ad.

I thought I might have a couple of responses to my ad from males but I truly didn’t think that I would have any interest from females. Within a week of placing the ad I had three responses from males but none from any females. We had all provided personal descriptions of ourselves via email to the others as well as a write up of what we liked sexually. Finally, in the second week I received, not one, but two responses from females. I wrote them and told them that we already had four males including myself who wished to participate, and I suggested a little get together the next week at a local coffee house just to get to know each other before we actually got together for a party.

We all agreed to meet around the bench in front of the coffee house at 7:30, and we were all to wear some sort of hat to help distinguish us. The allotted time came and I had arrived at the coffee house with a ball cap on as agreed upon. One man was sitting on the bench when I arrived about 7:25. He was about my age, 50, and a little heavier than myself, with dark hair and a moustache. He too was wearing a ball cap. I went up and said, “Hi, my names Larry.” He smiled and said he was Joe, who I remembered from the email descriptions. Initial contact was made. It was just a couple of minutes before a lady walked up. She was also wearing a ball cap with a ponytail sticking out of it in back, jeans, and a t-shirt. She was about forty with a medium build and an attractive but somewhat nervous smile. She introduced herself as June. Shortly Ken showed up, he turned out to be in his late twenties or early thirties, with sandy hair and slim build. Then Sandy popped in on the group. She was a vivacious blonde slim and quite attractive, and I guessed early twenties. The last male did not show by 7:45 so we went on inside got a table and ordered coffee and proceeded to get to know each other.

The conversation mainly centered around current events and weather at first until we began to get comfortable and it slowly evolved into a more personal nature with each person sharing a little about themselves, but each was careful not to divulge too much specifics, still being a little guarded. We were in a back corner of the coffee house, which was quiet this time of the evening so it was a fairly intimate location. Finally after we all became comfortable with each other, the conversation turned to another meeting. One with more intimacy. Ken suggested his place, since his roommate was scheduled to be out of town the next week. He said he would email those of us there with the address by Sunday. We agreed to exclude Allen, who had not shown up for this meeting from this next get together.

Sunday came and sure enough, true to his word Ken emailed his address. We had all agreed to meet at Ken’s at 8:00 Thursday evening. We all showed up reasonably on time. Ken had some snack foods and drinks available. Since we were all new to this we didn’t know exactly what to do. I finally suggested that we all get nude and proceeded to take my clothes off. We had all agreed that anyone could leave at any time if they began to feel uncomfortable. Everyone else began to follow suit, with the males being somewhat more enthusiastic. I piled my clothes on the floor and turned to watch the others undress. I think we were all somewhat stimulated by the sexual excitement in the air. We all anticipated what was about to happen. My small five-inch cock was partially stiff and hung expectantly. Ken’s younger cock was also semi-rigid and was really quite handsome and very large it seemed to me. It appeared to be approximately 8” in it’s current state and I imagined it would erect to around 9”. Joe’s penis was about the same size as mine, perhaps about an inch longer, but it was not circumcised so his foreskin covered the head. I was immediately jealous of both of these guys, Ken for his length and Joe for his foreskin, but hey, you have to play with the hand that is dealt you was always my favorite saying.

The girls had watched us get naked and now enjoyed the view. We three guys said that it was now their turn. June smiled and began to slowly unbutton her blouse. Ken went over to the stereo and turned up the music slightly to coax her stripping. She proceeded to dance and gyrate like a stripper and slowly discard her clothes. By the time she was down to her bra and panties all three cocks were at full attention. She noticed the effect she was having on us and smiled. She undid her bra in back and cupped her breasts while she slowly removed her bra. As she pulled it away she revealed a very nice pair of medium sized breasts with dark areoles and stiff nipples. She tossed her bra aside and reached down and slipped her panties down over her knees and let them slip to her ankles and kicked them off. We all watched her lovely breasts dangle as she did so. It indeed appeared that she was enjoying the display she was putting on. We all looked at the dark triangle of hair between her legs in anticipation of seeing more soon. None of us guys dared touch our now rigid cocks for fear of cumming so soon.

It was now Sandy’s turn. She seemed a little nervous but she reached down and grasped the bottom of her t-shirt and pulled it over her head. Her bra covered her small breasts. She took off her tennis shoes and socks exposing some nicely pedicure toes. Next she slipped off her jeans and she was down to her bra and panties. She reached around behind her and undid the bra clasps and slipped out of her bra exposing a very small set of breasts with nipples that puffed and jutted out declaring their predominance over the breasts. She then reached down and slipped her panties off, exposing her natural blonde pubic hair. Sandy mentioned something about being self conscious of her small breasts. We all assured her that they were lovely and I told her she should be a male and have a cock the size of mine. This brought a few laughs and broke the tension.

After a little discussion we finally decided to do this one person at a time. The subject would lie on the bed and masturbate while the rest of us watched. I suggested that the girls go first since it would probably take me about two seconds to cum and I wouldn’t put on much of a show. June volunteered. She went to her purse and brought out a battery-operated vibrator. It was a phallic shape with a small beaver at the base that had a vibrating tongue. A wire ran from the base of the shaft to a battery holder. It looked very similar to the one my wife used. She proceeded to climb on the bed and began to run the vibrator over her breasts and stomach. Then she lie down and spread her legs and we all grouped to the end of the bed to watch her spread her pussy lips and slowly insert the vibrator into her slit. She pushed the little beaver up against her clit area and her body began to press against her male substitute. We all watched in fascination as she very quickly exploded to orgasm. Her body thrust up off the bed and shuddered. The only other female I had ever watched masturbate was my wife and it had taken her several minutes to reach orgasm. I couldn’t believe how quickly June had cum. Not only did she cum quickly but she kept cumming having one orgasm after another as we all watched fascinated. Finally after about ten minutes of orgasms she stopped, exhausted and lay there on the bed smiling. Finally she gained enough composure to say that she had never cum so quickly before, and contributed it to the atmosphere.

Ken volunteered to go next, as June got up off the bed Ken took her place. He lay on his back and began to slowly stroke his large penis. I looked at the rest of the observers as he moved his hand up and down his rigid cock. Both girls had their hands between their legs and were fingering themselves while Joe and I just stood and oozed precum from our cocks. It took only a few seconds for Ken to shoot his load up onto his stomach and chest. A spurt even hit his face and since he couldn’t quite reach it with his tongue he reached up and slid it off with his finger and then placed his finger in his mouth. We all gasped some, obviously finding this quite erotic. Ken finally grabbed some Kleenex off the bedside table and wiped the rest of the cum from his body and dropped the Kleenex into a wastebasket. His cock had shriveled back to a normal size, well normal meaning about 4” soft.

I suggested that Joe and I masturbate while watching Sandy. All seemed to think that was a good idea. Sandy asked June if she could borrow her vibrator and June agreed and went into the bathroom to wash it for Sandy. She brought it back out and gave it to Sandy who had climbed onto the bed and lay down with her legs spread. Her light blond pubic hair appeared as an almost invisible fuss and her breasts were barely apparent except for the puffy erect nipples. Sandy wasted no time in inserting the vibrator between her legs and moving it back and forth. It was apparent that she was new to this so June sat down on the edge of the bed and said here let me helped and she touched her hand to Sandy’s. Sandy relinquished control of the vibrator and layback to enjoy the experience. Joe and I were barely stroking our throbbing cocks but I could feel the orgasm start in my body as I watched the lovely June sliding this vibrator back and forth gently into Sandy. I put my hand down below my cock and shot my load into it. I could hold it no longer. It was one of the most violent orgasms I had had in years. It was so completely satisfying that my legs almost collapsed under me. I walked around and took a Kleenex from the box and wiped my cum from my hand and dropped it into the wastebasket. I continued to watch the show and noticed Joe also spurt his sperm into his hand as I had. Ken was beginning to get hard again and I saw him begin to stroke his cock back to its full size.

It took Sandy about ten minutes to cum with June’s help but she finally had a tremendous orgasm and shook the whole bed with her shuddering body. Ken came for a second time while Sandy was cumming and I wished I were young again.

We all lounged around for a while before going through the process one more time. We all agreed that this was an extremely erotic pastime and agreed to get together once a month to enjoy our hobby as we dressed and headed back to our routine lives.