Bill,
Bill Patterson said:
She [Joanne] also told me that in the heat of his [Tom's] breast sucking, she [my woman friend, Jamie] undid his trousers and played with his cock. He came in her hands and she smeared it all over his cock and balls. .... They are going out again tonight for dinner....
Good for Jamie. It sounds like there's little doubt she will fuck Tom in the near future.
Bill Patterson said:
....but she has class in the morning, so no late night for Tom.
Maybe. Tonight is likely to be the night, in my opinion. Afterwards, Tom may take her home "relatively early" if she doesn't want to stay out too late. But hey, I could be wrong.
Bill Patterson said:
To Custer: The thought of actually losing her, knowing that I do now have a real rival, not just someone looking for a little fun, makes this an even more intense experience than I could have hoped for.
Yes, I would think so.
Bill Patterson said:
Should I relent and call her or should I play it cool and let her think I am not jealous of her dating? .... Part of me says pick up my cell and call her, while my cock and balls say let him have a clear field for "a while" and just enjoy the agony. What do you think, call now or call way later.
Hm.... good question. If you call Jamie sometime during the day before "date 2" and talk with her, and ask causally how it went with Tom but don't seem anxious about it, that may impress her with your continuing interest in her and your desire to verify things went well and she had a good experience. Women, almost certainly including Jamie, like to be called by men so that too would be a point in favor of calling her. (It may already be too late for that today, however. Or perhaps you've already done it. If so, I'd say you did the right thing.)
You should definitely not call her (in my opinion) while she is out with Tom. She would most likely interpret that as you hassling her with an expression of possessiveness, and as an attempt to let Tom know that he is out with "your woman." That would almost certainly be a strike against you.
I would suggest calling Jamie sometime during the day after "date 2" with Tom, whenever it's mutually convenient — not to express anxiety, but for the reasons noted above.
Regarding your reply to Sarena:
Bill Patterson said:
I do not believe that Joanne has a serious guy, it might be fun to date her in front of Jamie. I wonder if that would make her jealous or push her more quickly into Tom's arms.
If you start dating Joanne, Jamie is likely to interpret that as meaning you're taking advantage of her adventure, so to speak, to "fool around" with another woman yourself — and your desire to do that may even have been the motivation for you encouraging her to date Tom. She may even conclude it means her relationship with you is coming to an end. In either case, it would (I would guess) provide motivation for her to, in addition to fucking Tom, become serious about him as a possibly-preferable romantic alternative. In other words, you could lose your woman.
Thus, I suggest not fucking around with other women while Jamie is dating and fucking Tom. That is, until such time as both of you agree you want to maintain your relationship while both of you are free to date others. An agreement of this nature is something you might want to consider if Jamie's trysts with Tom are successful and she decides she wants to continue seeing him.
Regarding your more recent post:
Bill Patterson said:
I was just thinking. Since Jamie's only birth control are rubbers, her future, our future, Tom's future could be decided on the strength of a little piece of latex. Tell me if that is not something to ponder and jack off by.
I'd say that should be strong motivation for Jamie to go on the pill. Since she's relatively young, she should be able to do that safely for some number of years. If she doesn't like that idea, obtaining an IUD would be an alternative. (There are others.) Since you think the two of you may have a future together, it would not be out of order for you to discuss this with her and urge her to go on some form of reliable birth control *in addition* to condoms which she should continue to use, of course, for the usual reasons of safety — i.e., avoiding STDs.
—Custer