I was separated from my wife when this occurred. We got divorced about a year later. This experience has a backstory to it so I will relate the whole thing.
I didn’t have anything going as far as a relationship and I needed some female companionship. I found a site on the internet that listed a number of ladies available for outcall massages. I read over the various listings and picked one who sounded appealing. She was Japanese (so was my wife) and I was partial to Asian ladies so maybe I picked her because I was missing my wife. Who knows?
Anyway, she showed up at my door and was as attractive as her photos had shown. We seemed to hit it off and after giving her a tour of my house we ended up in the bedroom with me stripped naked and her in what I guess is called a teddy. I made no attempt at modesty when I stripped down and it obviously didn’t bother her in the least.
She gave me a very nice massage and of course it ended up with the usual hand job. Once she started stroking my cock, I had asked her to get naked too and she said she would but wanted more money. I didn’t think it was worth what she was asking so I didn’t go for it.
I saw her several times after that and we actually got to be quite friendly. I even took her to dinner several times and then we would finish the evening off with the massage. The massage part of the relationship was still strictly business and she stuck to her normal routine. During our time together she asked me a great number of questions about my sexuality and in the course of our conversations I mentioned that I had experienced a few sessions with a guy or in some cases, such as a group jack, several guys. This really interested her and generated a lot of conversation. She wanted to know all the details.
A week or so after our most recent get together she called me and said she had a strange request. She had another client who she saw regularly. This guy was some hot shot surgeon who was married but saw her on the side. In the course of their conversations he had told her that he was bi-curious and had a very strong desire for some sexual contact with a guy but was afraid to try to initiate anything. Or he didn’t know how to go about it safely. She told him about me and said if it was ok with him she would try to set something up with me and she would participate along with us, which might ease his concern. He told her to go for it and so this phone call to me was to find out if I was interested.
It sounded interesting, particularly with her being there to kind of orchestrate things. Plus the other guy was footing the bill, which made it even more interesting. She described to me a very elaborate scenario that she had conjured up. It had something to do with both of us guys being blindfolded with all three of us in the bed naked. We two guys would fondle and masturbate each other with her helping and then if it got to that, we could suck each other’s cocks. She had all kinds of variations of what might occur. She had me sucking his cock while she jacked me off and vice versa with him sucking me while getting jacked off.
The more she talked about it the more excited she got about the whole thing and it all sounded pretty exciting to me as well. Earlier in one of our conversations I had described to her about cock-to-cock jackoff, which she had never heard of before, but she was very keen about putting our two cocks together and jacking them both at the same time. I thought the blindfold thing was a little silly but I think she thought it would make it easier for the other guy since he was a first timer and a little wary of the whole thing.
So finally after a lot of conversation a date was set and we all agreed to do it at my house. An hour or so before they were due to arrive, she called to tell me that he had to cancel because he got called in for an emergency surgery. She later got him to confess that he had gotten cold feet at the last minute and couldn’t go through with it. And despite her attempts to get him to change his mind for a possible future get-together, he wouldn’t do it.
I was disappointed as it had sounded like it might be some fun and frankly I was kind of looking forward to a little cock play with another guy as I hadn’t done that in quite some time.
I had remembered that on the site where I found my massage partner’s listing there was also a listing for a massage team made up of a guy and a gal. So I thought I might try that and maybe I could get something going. I contacted them and set up an appointment.
They arrived at my house fully equipped with a portable professional massage table. The guy was kind of an average looking dude and had an open and pleasant manner. The girl was extremely cute (and Asian) and had a perfect little body. She had small breasts, which was fine with me, and terrific legs and ass. Also young….only 22 at the time. His name was Ray and hers was Gia.
So they set up the massage table and I got naked and lay face down. The guy stripped to just some shorts and she stripped to her bikini panties and no top. They both started working on me at the same time. This was a very pleasant sensation and it totally relaxed me. In fact I came close to dozing off it was so relaxing.
After quite some time I noticed that there were only two hands, not four, massaging me. I realized that it was just the girl’s hands on me. This was one of those massage tables that has a hole where your face goes so it was difficult to look up and see what was going on but after a while my curiosity got the best of me and I managed to look back and see that they were both now totally naked and he was fucking her standing up doggie style while she massaged me.
When I saw that I figured it was time for me to turn over which I did and she started in on the front of my body and quickly got to my cock which was now rock hard. He continued to fuck her while she jacked me off to a really terrific orgasm. I sprayed cum all over the place. The girl hadn’t had much to say up to that point but when she saw my cock spurting like it did, her eyes got as big as saucers and she commented about the amount and force of my ejaculation.
In talking to Ray later he explained that Gia was not his regular partner for the threesome massage. I had noticed that the photo of the girl on his website was not the same girl who showed up with him. He said when he got my call he had hastily recruited Gia to help him out but she wasn’t into this as a full time endeavor.
I saw this couple two more times and by the third time we were both fucking her. She did some cock-to-cock jackoff on the two of us at my suggestion. Neither of them had experienced that before. And then there was one session where she was sucking my cock and he was fucking her doggie style when I suggested he move over to me and I took his cock, wet with her juices, and started sucking him off. This really turned her on for some reason. I was in one of those moods where I was so turned on that anything goes. While I sucked his cock she really got it going on my cock and before l long I was shooting my load down her eager throat.
The odd thing about the guy was he never came. In fact, in the three sessions we had I don’t think he ever came. The whole sex thing seemed to just be something to do as far as he was concerned but it never appeared, at least to me, that an orgasm was part of his routine. I asked Gia about it later and she said she had never seen him cum either. Strange.
Anyway, that was the last time I saw them as a couple because one day she was partnered with him and the next day she was partnered with me and he was the odd man out. I am not even sure how it happened. It just did. A few days after the third time we were together Gia called me to say she didn’t want to see me with Ray again but wanted to just see me alone. So that’s how we got started. Of course Ray no longer speaks to either of us. That was six years ago and she and I are still a couple.
So shortly after carving Ray out of the mix, I was seeing her two or three times a week and no longer having to pay Ray for it. And I wasn’t paying her either. At this point my sexual level was at full charge and I came up with the idea of putting together a group jack although the new twist was I wanted my Gia to participate. She was hesitant but I could also tell that the idea excited her. Finally I got her to commit to being part of it.
I put an ad on the bulletin board of the Masturbation Page. I don’t think that site still has that feature. It later became a pay site. I think I also put it on Craig’s List. I had been involved in three previous group jacks, two that I organized and one that somebody else did. The ad attracted a lot of attention and I must have had ten or so guys who were all pumped up about being part of it. Having been through this before, I knew that the majority of these guys would chicken out and not show up.
This was several years ago and I don’t remember all the specifics but as I recall, I had eight definite commitments. I had a hotel mini-suite rented at a hotel near the Los Angeles airport. Because I couldn’t get the room number in advance to give to anybody, I had arranged for us to all meet in the hotel lobby where I gave the room number to everybody. I had told everyone that they had to be there by a certain time because at that point we would all go up to the room and if anyone was late, there was no way for them to know where we were.
By deadline time there were only four of us, counting myself. I waited an extra five minutes or so but everyone was anxious to get started so when no one else showed we went up to the room. I found out later that two other guys had arrived just moments after we went up to the room. They had both gotten caught in heavy traffic and to say the least, when I told them what had transpired, they were both very sorry that they missed out.
Gia was already waiting in the room when the group got there and I know the guys were quite impressed when they saw her. She is extremely attractive and was only 22 years old at the time.
One of the guys was probably 45 or so, another one was 30 and the third guy was maybe 25. All three appeared to be straight and two of them were obviously quite nervous. The older guy had been in a previous group jack with me so he was an old hand at it.
We talked for a bit and then I suggested that we get started. We all stripped down. A couple of us left a t-shirt on but two of the guys stripped totally naked. At first I could tell Gia was apprehensive about the whole thing. It had to be a little daunting for her with four naked guys with hard-ons. When she first stripped she kept on her bikini panties.
We all sat around in a rough circle jacking our cocks and I suggested to Gia that she jack mine for me, which she did. I noticed that the other three guys were intently watching her stroke my cock so after a few minutes I whispered in her ear and suggested that she go around the room and give each guy some stroking.
By now she was getting more comfortable with the situation and she moved over to the guy next to me and took hold of his prick and began to stroke him. This guy had a cock that was almost an exact duplicate of mine. I have never seen a cock that looked so similar. I wasn’t the only one who noticed this as Gia commented about how alike our cocks were.
She spent about three or four minutes on the guy’s cock and then moved to the next guy. She repeated this as she moved around the room. By the time she got back to me, she realized that she owned the room. These guys were all her slaves. By now she was really getting into it. I suggested that she take off her panties and she eagerly stripped them off. She has a fully shaved pussy and it is a damned good looking one and everybody in the room immediately was focused on it.
She started jacking my cock again. I looked around at the other guys. Two of them were stroking their pricks while intently watching her stroke mine. The third guy wasn’t touching his prick at all. He later told us he was so turned on that he was afraid he would cum if he touched it.
I really wanted to get my fingers in her pussy but I had previously told all the guys that there was to be no touching her. So I figured I had to play by my own rules.
Again, after spending a few minutes masturbating my prick, she moved on to the guy next to me. This was the guy with the similar prick. As she jacked him, I suggested that we try a little cock-to-cock. I could tell that he wasn’t too sure about this but was probably afraid to say no. Maybe not afraid, but just concerned not to mess up the rhythm of what was going on. So the two of us stood up facing one another with our two identical cocks pointing to the ceiling. Fortunately we were about the same height so our pricks lined up nicely.
The older guy had brought a tub of lubricant that we all shared. Gia took a swipe of the stuff on her fingers and proceeded to grab our two cocks and start jacking them together. I had previously told her how to insert one finger between the two pricks as she grasped them so that her finger rubbed on the underside of both cocks while she jacked us. It didn’t take too much of this before both of us guys realized we were about to spurt and neither of us were ready yet so we called a stop to the cock-to-cock action at that point.
Gia continued to make the rounds of the group, jacking each of our cocks in turn. She was totally uninhibited giving a running commentary about each guy’s cock while she jacked it and asking what felt good and was he about to cum and so on. She paid no attention to the fact that she was totally naked and in some of the positions she got into to jack each guy’s prick, her pussy was fully on display and I noticed that it was very, very wet.
She confided in me later that she had experienced several orgasms while jacking all of our cocks. And I believe it looking at how wet she was. She is pretty orgasmic anyway and it doesn’t take much for her to cum.
After she had made the rounds of the group a number of times it was obvious that we were all ready to cum. I suggested to her that each of us lay down on the sofa in turn and she could jack us to orgasm. Since at this point she was back to stroking my cock, I elected to go first. I lay back on the sofa and she straddled my legs on her knees. By spreading her legs, this opened up her pussy to view. I noticed that as we got into position the other guys jockeyed around to where they could see her wet cunt from behind.
She started to seriously jack my prick and it didn’t take too long for me to cum. At that point, we had all been either jacking our own pricks or she had jacked them for us for well over an hour. So before long powerful jets of semen began to spurt from my cock. The wet juice splattered all over my chest and even my neck and face. Gia really knows how to jack a cock and continued to pump me until every last drop of cum was coaxed out of my prick.
I had brought a supply of hand cloths and she took one and wiped all of the cum off of me and also very carefully wiped my dripping penis clean and dry. After I lay there for a few minutes I got up and the next guy took my place.
She proceeded to repeat the whole process. As she jacked his cock she had a running commentary going urging him to cum for her….to shoot his cum for her…to make that big hard cock spurt for her….and so forth. Of course it didn’t take long and the second guy was shooting a wet load all over himself.
She took another cloth and very carefully wiped him clean taking extra time to caress his dripping cock, squeezing a few last drops of cum out of his wilting prick. As she wiped the cum off the head of his prick, she cupped his balls with her other hand and massaged them.
Then it was the older guy’s turn. He didn’t last long either as she repeated her ministrations to his prick. I noticed that while she jacked him, she had just one of his legs between hers and she was rubbing her pussy on his leg. From the look on her face I am pretty sure she came about the same time he did. He kept telling her it was the best hand job he ever had and thanked her over and over.
After he came, she held his prick in one hand and wiped up his cum with a cloth in her other hand. While wiping his cum she continued to slowly milk his penis. She took her fingertips and massaged the head of his cock. This was obviously a little too intense because he had to push her hand away.
Finally it was the turn of the fourth and final guy. This is the guy who had refrained from jacking himself while she jacked the rest of us. He also had the smallest cock of the group. I don’t think it was even five inches. But despite his concern that he might cum prematurely, he took to longest to actually spurt his load. And when he did, it was in proportion to the size of his cock. It was just a few weak little spurts. She held the head of his penis between two fingers and rubbed it up and down and squeezed it which coaxed some more drops of cum out of his prick. I could tell she was getting a real kick out of playing with four different cocks.
After we had all cum, we just kind of sat around exhausted with our now deflated pricks resting on our thighs. A few stray dribbles of cum trailed out of a couple of the cocks. Gia took some hand cloths and went around doing some final clean up on each of the drooling penises. She would take hold of each cock while she wiped the head clean and give each one a loving squeeze before she would let it flop back down on the guy’s leg.
I was impressed with how she had enthusiastically gotten into the whole scene and had given some personal attention to each guy. She later told me that after her initial concern, and she realized that she was pretty much in control, that she totally got on board and had a really great time. All the guys were gentlemen and nobody said or did anything out of line. They all profusely thanked her afterwards. All in all a very fun and civilized experience for everyone.
After we got back to my house, we were both still incredibly horny and ended up having a wild session. She told me later that the group jackoff thing was incredibly erotic and exciting for her. She said she was nervous at first but once she realized that she was running the show it gave her a feeling of tremendous power on top of the erotic charge of having four hard cocks to play with.
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