Sunday, March 30

Should I let his trainer hand-job him?

david is stripped fully nude for his weigh-ins by his trainer whether he likes it or not. And even now, after this having been repeated dozens of times, it's true that he still sprouts an erection. We always tease him about his erections, because it's really him getting excited by submitting to a woman, even if it's his young physical trainer of all things who is about to (quite literally) kick his ass!

I write today, because Michelle is very happy with david's progress. She has earned herself another bonus and david is looking very fit. She offered that really david should be getting a reward. I asked her what she had in mind. She suggested maybe a hand job or a nice ass fucking. I asked me or you? She said, "either way" so long as it's what I wanted and so long as I was present. She could watch or she could do the honors while I watched. Well that sounded very non-threatening to me.

Let's put it to a vote, why don't we? Those are the four choices:
  1. hand job from me while Michelle watches,
  2. hand job from Michelle while I watch,
  3. gentle anal sex with a strap-on from me while Michelle watches,
  4. gentle anal sex with a strap-on from Michelle while I watch.
Whichever one of those 4 options you choose, you can also suggest some embellishments such as what the other person should do while this is going on, his outfit, a spanking before or after, the position we should put him in, a relevant preparation for him, and so on.

Let me know. Majority rules!

88 comments:

  1. Oh my, number four for sure! Thanks for letting us vote. Panties only and then pulled down, but not off. I have no doubt Julie will figure out the best way to show off his spanked bottom as he is pegged.

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    Replies
    1. A good pegging from his trainer. He would enjoy that!

      Delete
  2. Number 4, after a spanking with the hairbrush
    j

    ReplyDelete
    Replies
    1. Yes, he should be spanked, always.

      Delete
  3. you could do strapon from yourself while Michelle gives him hand job

    emily,

    Then with all those bonuses and david getting smaller I am sure he would need a new smaller more feminine wardrobe. Has Michelle seen his inserts yet?

    emily

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    1. I'll count that as half for 2 and half for 3

      Delete
  4. My vote is on number 4, but of course, classic pre-warm spanking given by Ms. Julie, refreshingly new strap-on gentle fucking by Michelle and if he cums in less than 5 minutes, send Michelle home and have your way with him Ms. Julie.

    Regards,
    Manny

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    Replies
    1. He won't cum from the pegging alone. He needs clit stimulation. so no spurty for poor davey?

      Delete
  5. Thank you for the opportunity of voting. I suggest gentle anal sex from you with Michelle watching. Only you should administer rewards for his good behavior.
    Respectfully
    Stan

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    Replies
    1. A nice thought, but I control all, and if he gets anything from Michelle, it is because of my will and my will only...

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  6. Miss Julie:

    My dominant has only revealed what we do to one of her co-workers (Liz). Liz has watched me do housework in my maid's uniform. I have served tea and Liz has been allowed to cane me (Ouch!).

    I respectfully suggest, after a spanking or better yet a true caning, that you mount David and take him annally while Liz wears a strapon that David takes in his lipstick wearing mouth. Liz has mentioned that this is the absolute ultimate in female domination: a cute male in an adorable French maid's outfit, on his hands and knees, being taken by two dominant women - one mounting him anally while he services the other just like an ultimate girly girl with his mouth.

    As the sissy in this situation I can tell you that being on your hands and knees and having your skirt and petticoat lifted up over your back is, all by itself, a trip deep into feminine subspace.

    I suspect all three of you would enjoy this scene immensely.

    Respectully,

    Miss Raquel
    Sissy Maid

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  7. 2 and 3: Gentle anal sex from you while Michelle give him a hand job. The anal sex stops the moment he orgasms. It is a reward after all.

    Otherwise: 4.

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    1. What if Michelle is having fun up in there? Rude to have her stop just because he cums. He would have just have to grit his teeth and see it through.

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  8. 4, dressed as a sissy, blind folded, on his hands and knees, while eating you.

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    1. No eating in front of Michelle!

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  9. Julie, I think you should have Michelle give him a handjob, but have her do it through his work out clothes or his undies and shorts. You could have her tease david through his pants until he loses control and cums in them (after all, im sure you dont want him enjoying another lady's hand on his cock TOO much). That way he gets his reward, but also learns a lesson. Plus you can always tease more fun if he continues to do well.

    Jimmy

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    Replies
    1. I like it! I might have pass this time around, deferring to the vote, but definitely to be kept in reserve. I like things that are reward and reminder at the same time. I imagine Michelle would make him workout in his cummy pants!

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  10. I dont think he should take any pleasure from his coach. There fore i suggest no handjob and no anal strop on from her if he feels pleasure out of it. At the maximum i woul allow some excercise wich use his anus like leg press on top of a nice plug or climbing the stairs when plugged. You are his wife and the only one he should think of and associate tompleasure.

    Ss

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    Replies
    1. I like the power of granting him another woman, though, or denying it to him!

      Delete
  11. I think number 4 would be appropriate but only if you were at the other side rewarding his mouth with your own strap-on!!!

    I love your blog and have you linked on both of mine, I'd love it if you could link my blogs too, check them out at:
    http://sissykaaren.blogspot.com/
    http://sissykaaren2.blogspot.com/

    ReplyDelete
    Replies
    1. Yes, I like that!
      I'll be happy to add you to my blogroll.
      But why 2 sites - they seem quite similar in nature?

      Delete
    2. I had some issues with Google+...they were shocked that I had posted "Adult Content" so I started the second one as a "just in case" kind of thing. Just in case the Google police flushed me down the memory hole!
      I update both daily and would dearly appreciate your consideration.

      Delete
  12. Dear Ms. Julie,
    I rather agree with Miss Raquel- i think it would be perfect to have david in her bra and panties (and maybe a pretty pink babydoll nightie!) wearing at least some perfume and a little blush and lipstick taking Your cock in her mouth while she is taking it in her behind from her trainer! i think david would enjoy this very much (i would!!) especially if she were allowed to cum in a glass and enjoy consuming it for the entertainment of the Ladies! Oh i am so jealous of david!
    Curtsy,
    sissy jennifer

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    Replies
    1. Oral and anal... a popular choice...

      Delete
  13. I think 3 for me Maam as I kinda have trouble seeing you in anything less than a dominant position Ms Julie.

    I'm also a little concerned about the 'all over too quick' problem. Perhaps david might receive some strokes to his rear for every minute he is under a target time. Clothing wise im dieing to hear about david training in a short pink skirt. This is way overdue. A quick lap of the outside of the house would be fun for him too im sure.

    A lovely idea Ma'am to invite suggestions.

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    1. Vote noted, lill jo. Now, I believe you have a chore to do for me and some photos to send?

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    2. Yes Maam
      I am sorry for sending you a photo of me in manly clothes Maam. Totally inappropriate for a pansy boy like me Ma'am. I have spanked myself hard as instructed Ms julie and sent more appropriate photos Ma'am.
      *curtsey*
      lill ( Ms Julie's punished sketch slut ) jo

      Delete
  14. I think you should both put on a strapon and one of you should be on the front and one on the back and you can spit-roast em! Personally I would think the trainer giving it to his bottom and Miss Julie having him suck her strapon would be ideal, but either way.

    I think that would be, by far, the hottest. I know it is my fantasy.

    ReplyDelete
    Replies
    1. You may just get your wish the way the voting is going!

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  15. I vote #4, followed by a good spanking to remind him who his ass belongs to...

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  16. I would vote for a handjob from Michelle whilst you watch. As a twist I would ensure she stops just before he squirts to make it a ruined orgasm - and obviously he would have to drink it all down!

    Deni xxx

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  17. Hi Julie,
    Since this is a reward...
    I vote for #4....and as others have mentioned, a Spanking,
    Butt a nice OTK from Both of you.
    Every Sub love's a nice ( Non Punishment) Spanking to
    put them into Sub Space...:-)

    As to what you could also do...
    Hmm.. How about Milking Him at the same time?
    I think you already have an idea as to what to do with
    his Orgasm....:-)

    Great Post as always,
    Hotbottominnj

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    Replies
    1. I won't be a punishment spanking, but his eyes may get a bit wet...

      Delete
  18. david would be dressed in his best naughty schoolgirl outfit (complete with plaid miniskirt, panties, pantyhose and "come-fuck-me heels). You would begin by giving him a hard otk paddling with a spencer paddle. Michelle would then have him on all fours to present his ass. She would proceed to fuck him while You are on Your knees in front of him with Your pantied ass pressed against his face. You would then pull Your panties down and david would be forced to lick Your asshole while Michelle continues fuck him. You tell him "no pussy for you. The only pussy that's getting dealt with is yours". When he cums You make him lick it up. You would finish by making him watch as Michelle eats Your pussy all the while telling david he's not worthy of the honor Michelle has. Don't know if You like the last part but it would add to david's humiliation.

    ReplyDelete
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    1. I like the hard paddling.
      I like the subservience of the ass licking, but I don't want to be bare in front of Michelle!

      Delete
  19. I think Michelle wants to ass-fuck him and should be rewarded for her training.

    So I'm voting for #4. Miss Julie might sit on his face and hold his legs while he's taking it up the ass. That would certainly be what I wanted were I David;)

    tomas

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    Replies
    1. I like that. I can sit on his face in my tight yoga pants!

      Delete
  20. It is possible that Michelle has never had the opportunity to use a strap-on and would like to give it a try (forgive me if I have not read previous posts about her with appropriate scrutiny). So I vote for number 4.

    If you and she were up for it as a follow up, I would suggest that he be allowed/required to lick her pussy while you whip his bottom or fuck his ass yourself.

    It sounds like Michelle is game for enhancing your relationship in a respectful way.

    Enjoy yourself,

    -Rosco

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  21. Number 2 for me. Wow what a reward handjob from his trainer. A.W.

    ReplyDelete
    Replies
    1. Not a popular choice, but one I suspect david would like best.

      Delete
  22. Definitely #2 hand job from Michelle while I watch. Of course you should be teasing him and spanking him while it's happening. And then have Michelle ruin his orgasm when he starts cumming and you spank/paddle him REALLY HARD as his cum dribbles out. No mercy!!!

    ReplyDelete
    Replies
    1. This one appeals to me. Paddling his ass HARD as the cum dribbles!

      Delete
  23. Does david enjoy gentle anal sex...i.e. will he orgasm from it? If so, make it a 'contest' of sorts - if he's able to hold off cumming after x minutes of gentle pegging from you, he gets a handy from Michelle. If he doesn't, no handy and a caning from Michelle. Of course even if he wins, he loses...

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    1. He enjoys it when done gently, but he will not cum from it. He usually gets soft, in fact, despite being aroused by it. Strange!

      Delete
  24. Julie,

    This is very hot. I vote for 4 and think that Raquel's suggestion has a lot of merit. If a handjob wins the vote i would blindfold him so he would never really be sure who did what. As far as the outfit I have one word....flashdance!

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  25. Hello,
    I say 4. david spanked by both of you just to warm him up. He should be in bra and skirt. If you have garter belt and hose with heals. Now as she rides david, he should be servicing you. The fucking last until you come 3 times.

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  26. May I suggest a combo? I would say that he should get gently done anally with the strap-on dildo by one of you two while the other gives him a handjob, so that he feels an orgasm while being penetrated. That should be quite humiliating!

    I don't know about the position - perhaps have him on the back elevated and knees drawn to the chest, so that he is nicely open, or simply kneeling with the butt in the air.

    I would also suggest having Michelle give him a little spanking and an enema before the dildoing.

    ReplyDelete
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    1. Enema is a great idea. I think it would embarrass me if he made a mess with Michelle!

      Delete
    2. The most important in my proposal is that he should have an orgasm while being fucked (or finger-fucked), so that you can tease him that he liked it back there...

      Delete
    3. Oh, I see! Missed it this time, but I like that concept!

      Delete
  27. Since this is a reward for excellent work, I vote to let David choose!

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    Replies
    1. Ha! Like that will ever happen!

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  28. I also vote #4 while you sit on his face & hold his legs open.

    ReplyDelete
    Replies
    1. Can i sit on his face in my tight yoga pants?

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    2. darling, whatever You do will be okay with us;)
      tomas

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    3. Mmmm... Thank you, daddy!

      Delete
  29. Hand job is a reward isn't it ? You can finally feel relief from the sexual tension of the whole scene. It sounds a bit too mainstream porn for me
    We are more sophisticated that this! So I vote anal... while Michelle watches. just because I'm trying to imagine what I think would be worse if it was me
    I vote 3 !! : )

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    1. I can feel that. A Very ceremonial fucking from me. Maybe in the living room with him in skirt and blouse, bent over the back of the sofa. Make him raise his skirt and lower his panties for the penetration. Make sure Michelle has a good view as he takes every inch up his bum. Let her see first hand how much he's my little bitch...

      Delete
  30. Number 4 with a twist. I would have you both spank David in a humiliating fashion then have you fuck David with a strap-on while Michelle strokes him. To finish it off, while doing so, there should be some light banter between you and Michelle about how easily he's taking your strap-on and just how turned on he's getting. A comment or two about his manhood or his current situation would be icing on the cake. Needless to say he needs to clean up all the mess he makes. Perhaps have Michelle feed it to him by rubbing another dildo in it and making David clean it off.

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    Replies
    1. That's a given. My house rules is that he consumes EVERY DROP of cum that releases from his little clit.

      Delete
  31. This is a reward. No.4. No spanking.

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  32. An alternative in case the two-woman combo is impractical: have her stroke him with one hand while having two gloved, lubricated fingers of the other hand up his butt, feeling his prostate. Again, the goal is that he cum during penetration, so that you can tease him about his liking being penetrated.

    If you do him anally (with dildo or fingers), I suggest preventing him from ejaculating a number of days before the event (no sex, no wanking...). This way he will get a better prostatic experience. :-)

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    1. A finger fucking up his bum. Very creative!

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  33. Number 4 for sure. I would make sure David gets a nice spanking first though.

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    1. I agree with the spanking. He must ALWAYS be spanked.

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  34. Following a moderately severe spanking, I would choose #4.

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    1. I like where you're going with this. Maybe kill the "moderately".

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    2. aww, Julie,
      give the poor guy a break!
      we're all in favor of a spanking from both of you, but let him get turned on; don't kill his sexual buzz. It'll be more fun if he's all revved up -- then maybe he'll squirt for Michelle.
      -tomas

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    3. My husband is a strange creature. The harder I spank, the more turned on he gets! (Maybe not at the exact moment - in fact he tends to go all soft when I am strict that way - but as soon as I let him up, it's back again!)

      Delete
  35. Tell him he can have his fantasy of a handjob from Michelle.

    But at the same time, in exchange for this huge favor, he has to, and will, fulfill one of your fantasies. Suck a cock in front of Michelle. And since she's is married, and has to get permission to do this, it might be Michelle's husband's - his first real cock, or it might just be your strapon. But he will be blindfolded and never know. And its up to Michelle's husband. If its a fake cock, I suggest getting a new one that squirts and has pubes to make it extra real.

    And of course he will be spanked until the cock comes.

    -Al



    since she is married,

    ReplyDelete
    Replies
    1. Not practical. I can't cross this line (yet!)

      Delete
  36. Hello Ms. Julie,

    I like option # 4. But if you first put David into some appropriately sissy type attire, then lay him on his back. Lift his legs up in the air and then sit on his face, holding his legs up and back under your arms. This will make his little sissy hole easily available for Michelle's strapon. In addition, with your ass on his face, he will not be able to see what is going on with his stiff clitty.

    In this position both of you could alternate stroking his little clitty. But the rule might be that only you are allowed to actually make him squirt. So if he cums with Michelle's hand on his clitty, he will get a hard paddling afterward.

    To confuse his poor little mind, perhaps each of you could alternate hands and angles of clitty stroking, so he really cannot figure out whose hand is on his clit at any given moment. Again, with your ass planted firmly on his face, he will sightless as well. So even as he spurts, he will not know if punishment is to follow or not.

    Since he would not truly know which hand gave the final tug, you could even spank him either way. Just tell him he spurted at the wrong time and soiled Michelle's hand. She could even be the one to feed it to him, to "prove" he deserves the paddle.

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    Replies
    1. I like it! We could even paddle him in that position as well. One of us would need to hold his private parts out of the way, of course!

      Delete
  37. Number 4, but also she gives him a hand job, but yes well spanked first.
    Always
    Ron

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  38. Make it a real reward, give him all 4.
    While Michele is giving him the hand jOb, you should be fingering him to assert you authority.
    Also while Michele is ass fucking him, he should be licking you feet & toes as a sign of gratitude for letting him have that.

    ReplyDelete
    Replies
    1. All 4? What a sexual glutton you are!

      Delete
  39. Basically #1 - you give the hand job, Michelle gets to catch it and decide how to feed it back to david. Paint his lips with it, make him lick it off the dildo as suggested by another commenter, or even have him lick it off you while she teases him that the cum is from your lover. ;)

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  40. Wat too late to chime in but I love a long sound spanking on my panties and then a hard hand job.....
    Always
    Ron

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  41. Have the trainer use the strapon and you watch

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