Shemales, best of all worlds and greedy? or head fuck?

I am not sure I get shemales. Not because I have a prob with them. But I find it all confusing. I haven’t got an issue with anyone being who they want to of course. I just find it a head fuck!

The reason I am saying this is to do with a regular I chat and cam with. This chap likes to meet couples for sex. He is the classic sissy bitch who likes to suck cock and clean up. He always wears lingerie when I see him and always brings toys for me to direct the use. I get him to spank himself with a riding crop. Which I made him buy. I also ask him to beg on his knees to wank his cock, I control when he can touch it. I also do a count down to cum. He isn’t allowed to cum before I say.

He is attracted to both men and women for different reasons. Men he loves for cock and cum. Ladies he loves femininity and breasts. I have large breasts which he tells me he loves! He does talk about licking and sucking them. But mainly when we have our chats he gets very aroused by being used by men. He loves the thought of a cock in his arse and his mouth, While other men wank over him. He likes the thought of making a cock hard for me to fuck.  So It came as no surprise to hear him say he has recently fulfilled a fantasy by having sex with a shemale. He described it as mind-blowing!! the best thing he has ever done!

Each to their own I say but I cannot get my head around it. Is it either extremely greedy? Do you get the best of all worlds? its such a confusion for me. The jury is out in my head, I am just not sure! argh head fuck!

17 thoughts on “Shemales, best of all worlds and greedy? or head fuck?

  1. We don’t mind looking at the pics of them, they can be really beautiful but no HRT for this Sissy. Sure help ya look better, help with hair growth but we decided no. Sometimes I’d love the boobs tho but we can’t go out in small community with me totally feminized, I’m always shaved,smooth everywhere, eyebrows even done only wear panties. But my complete dress/ public humiliations by Mistress only done out of town. Clit usually locked also

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    1. Stunning some of them! But I can imagine the HRT etc can be really hard work. I live in a place called Manchester in the UK. Noone who bat an eyelid here if you were fully fem, it’s so annoying that people have to place their own restrictions on how you choose to live your life!

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      1. We live in Indiana , a town of 2500 , plus family.. My Mistress/ fiancé knows, started this of course, my and her best GF, my sister.. we have most of our fun , well my full dressed, submission at home and out of town, like I said tho at all the family stuff, around the community, I may be in pants but am fully shaved, lotioned, panties, usually chastity. Helps always remind me of my place, feel the panties, the chastity device and of course with those you have to sit to pee, even without the device when not using it, soon as we started was a rule I had to sit to pee, never really cheated either, helped with my training, submission. In Summer tho wear shorts all the time, no one has ever mentioned my legs always being shaved… Stephie


      2. I love chastity devices….control even where you’re not there! I used to have a lingerie shop, I have a fascination with fifties lingerie. I love a guy in seamed stockings! Does your mistress have a preference?

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  2. Yes we do look at shemale sites, etc. want to hear something funny my thing my whole life was lesbians, lesbian porn, even had some 3 some with bi girls. Kept trying to force lesbian porn etc on my fiancé before we started this. Haven’t looked at any lesbian porn sites since, pics etc.. we nosy watch sissy porn and some BBC cuckold porn, she likes that tho we will never do cuckold, to each their own. I strap on her 9×3 real feel no 7 BBC vibe over my clit when she orders it. Whole time she s saying sooo glad I made you my sissy, your cock is so small better as a clit and let me enjoy this. Turns us both on .. she craves power, dominance, I crave feminization, humiliation. It does help that I have a pretty small penis, bothered me for yrs but now helps with the way all my panties fit . Stephie

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      1. Not really, no panty hose tho, she wants me in garter belt, usually a 6 strap one, thigh highs diff colors, whatever she picks, sometimes seamed, some wide banded florals at top . Our sexual service sessions she always picks the lteddy, nightie, dress , bra, panties, stockings, garter belt. She’s good to me tho if in chastity always unlocks me for service session, likes to watch my sissy clit get hard when the stockings go up my legs, attach to my garter belt then slide on my panties. Likes to laugh as I’ve said and say you were born to be a sissy sub, mine ! We are going to go to better more realistic silicone breasts soon, C cup now, going to go to D.

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      2. It was a process . She wanted to try, had read some femdom on the net, is dominant anyway, likes power, control, I was already deffering to her guess she wanted to see if she could do the ultimate, full domination, submission/feminized me . She did, another huge power high she’s gotten from this that never ends. Definitely larger breasts and she wants larger nipples, we’ve found some , very realistic, role reversal again, like a man she likes to come from behind squeeze my boobs say how’s my gurl, squeeze my boobs when she takes me with her strap on , saying your tits feel great sissy girl but need to be bigger. I can go braless during sex by using spray tac, forget exact brand but just as good as medical adhesive and whole lot cheaper. And yes the further and further I went into submission/feminization the more I wanted to do anything to please her. Being locked in chastity for few months never hurt the submissive sissy male either, does wonders in helping them be obedient! And tho I’m let out for sessions wouldn’t dare cum without permission or could be locked up very long time! She’s good to me tho even if I’m not allowed to cum, she will let me finger my sissy clit, she will rub a vibe on my former balls, tho that’s more tease I think, pre cum allowed, can’t control, yes she will put on her finger and I will lick off, more power, control for her. And as I said when I use her strap on and toy on her those bullet vibes make my clit feel awesome. Since this began see she has trained me to think, feel pleasure sexually as a woman. It’s worked well. Chastity prob helped that along but I haven’t stroked my former penis in over a yr and a half! Learned to cum by fingering, her strap on. Barely remember cumming as a man in anyway! I am what she’s trained me to be/ made me. Guess it must have always been inside me somewhere. Yes I belong to her. Not partner etc. Belong, controlled sissy sub. Sorry if too graphic say so if I am. Sharing real experiences, maybe some reader will be interested or woman that wants to have a sissy sub. Stephie

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      3. She says so, loved taking me further and further into submission/feminization. Controlling when how I cum, all the chores, doing everything she says everywhere, especially the bedroom. She says it was one of the best sexual experiences she ever had when she first started breaking me in, taking me with her strap on and cock! Having me suck it to. Role reversal power I guess. The harness does have two front pockets with bullet vibes but she says that wasn’t why she came so hard the first time, it was the power of breaking me so to speak to how sex was going to be from now on, my sissy pussy was hers now she said, never forget it!

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  3. Now I do, was told to study, learn share. Tho the humiliations are very arousing and we’re in the beginning but they were sooo embarrassing, humiliating harder over a year ago. Had lots of training, further feminizing, submission inow into this over a year and a half.

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  4. Thanx a lot . Got late start today. Was laying in bed with Mistress blogging, sharing here . Our session ended at 6am for me this morn. After she’s had her service, orgasms, done with me , she goes to bed, I clean master bathroom, put out candles , put away , straighten the bedroom up, clean all the toys, check batteries, wash my lingerie, hers, clean the strap on harness. Get the make up station, have a big vanity like thing with lights, drawer compartment container, things, all our make up , brushes etc go in certain drawers. We have a lot! I’m responsible. Yes we do enjoy very much ,resisted in beginning but now I really try and look as feminine, even sexy as possible for a service session for her but I’m never going to look as good as these tumblr sissies, others… she’s happy . She’s a full figured woman I guess you’d say, but CONFIDENT, Dominant and Ifind this as sexy as a 18 yr old perfect figure girl in a bikini. I dated those types in my old life.. wouldn’t trade my Mistress/fiancé for any of them. She’s a professional woman in her 40’s . My training now has been such that I respect, defer to all women . Always courteous, respectful, submissive in mannerisms. Femdom teachings, sissy tracing teaches that women are the superior sex. I agree with this after a yr and nearly 8 months training. Oh just now in a strawberry scented bath. Mistress long asleep. When got going today finally, did, laundry, cooked dinner, dishes, ran sweeper. Did the shopping. I have her outfit for tomorrow already hung out, shoes, bra, panties even. She tells me which if each . They’re ready. I’m going to do some shaving, nail, lotion put some panties and nightie on and surf net awhile longer . Be up to cook her breakfast, I’m allowed a nap tho after that. I work part time. May paint my toes😊


  5. New experience for me last night after 2 months in chastity or as my Mistress soon to be wife calls it my clitty cage, after a full sex service session where she had several orgasms several ways she switched her toy from the strap on harness and instead of the usual dildo she fucks my sissy pussy with she had a new one vibrating ejaculating dildo. First as usual I was ordered to my knees sucked it she shot load on my face,all over. Then she reloaded it and fucked my sissy pussy relentlessly, then said cum sissy, I ve been able to for good while now from strap on fucking alone. So I came hard and she shot big load in my pussy ! It was awesome! Intense! I shook. Then I cleaned up all my cum , swallowed. The fake cum smells tastes pretty real. Just sharing

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      1. Thanx so much Ms. Curtsy. And thank you for addressing me as ” good girl” I am well trained aa my future wife’s SISSY by now , almost 2 yrs and Sissy, Stephie , girl is all she ever refers to me as, and myself included along with my anatomy parts are always ” clitty ” And ” pussy” last night with the ejaculating dildo I felt even more sissy, feminine than ever. Again that for your affirming comments . Stephie


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