by silkstockingslover
As usual, this was fantastic!
Why not choose to do both... maybe he needs to be feminized first and then pegged. The next chapter could be him coming to grips that he is a sissy who wants to get fucked by real cocks.
Hope to read the next chapter soon!
definately feminize him further humiliation and then strapon play
My choice is definitely option 1. I can't wait to see him be "turned" further and further ...
Option 1, please. And I'm hoping they secretly record him sucking Eugene, selectively sharing the video to further humiliate him!
option 2 pleaaaase. he must learn how pantyhose is great and how every sissy faggot need to wear them every day and in every occasion
every sissy faggot LOVES pantyhose
Love these stories im new to men and love it and these stories are amazing makes me with i was him, in my opinion start with option one then have it become the 2nd also have it so is no longer sexually attracted to women and becomes gay <3
Feminize him. I wish it was me. Loive to dress and am jealous of his cocksucking
Love this!! Defo option 2 as being a sissy means dressing like a girl!
start with option 2 eventually leading to a good ass fucking in later chapters
I think option 2 is a good next step, since he's been watching hypno vids starring sexy women getting all the cum they want. And Eugene may not want to have sex with a man, but a feminized sissy? Rose might introduce the pegging as Brian gets sexier and sexier for Eugene. Before you know it, we have a full on sissy cumslut in sexy femme style. Something Rose and Eugene can both enjoy.
Not full dressing, just panties and maybe girly socks, then pegging, then full dressing, then real cock
What a great day for jerking off. New stories from you and BJ Michaels on the same day. My two favorites. Wow, my cock is so sore, but a good sore.
Hello, and once more a great story. I would prefer option 2 that would lead to option 1 anyway...
I realy like the idea of him getting pegged by his girlfriend in front of audience (maybe Eugene) to ad some humilation.
And i would like to see him getting his ass-fucked by real cocks while he is wearing panties and girlsocks. But i wouldnt do the full feminisation on a muscular jock.
Have a nice day :)
Option #1 is where I want you to go. I'm more interested n reading about him becoming a real cum dump than having him get all dressed.
Since he isn't supposed to call the black man until after viewing these videos, they should make him more submissive to cocks in general and black cocks in particular. Have him opening his ass with dildos and butt plugs and craving something in his ass. Pegging and taking real cocks are the logical next steps. Once he is getting fucked like a girl, then the next step would be sissification with panties.
Definitely option #2: stockings, garters and heels. All made up like a gurl and then given poppers and pegged while he performs fellatio on a real man.
I'd like to see this go the way of Option 1: pegging and later on getting fucked.
storylines you have EVER created. And with the fantastic stories you have posted that says something! But wow. Option 1 or 2??? I think a mixture of both. My reasoning is, as I have mentioned before I am married to my Mistress and have been for years. All my Mistress would have to do is point to the floor and I would gladly suck a cock (which I have done) or take it in the ass (something I wish we would do). I also have a few pieces of lingerie that my Mistress likes for me to wear. The problem I have with option 2 is that I really hate makeup. I don't even like for women to wear the warpaint. So I would like for Rose and Brian to be in a loving committed relationship (married would be good, especially when she pegs him on the honeymoon while he's wearing a wedding dress), where she i9s in complete control of the family. A little cuckold thrown in for fun.
And BTW, I don't know if it was intentional or just something that fit the story, BUT! I am a 62 yrs old, 6'7", 360lbs, a retired cop, and will soon be a retired truck driver in a few years. NEVER be ashamed of who you are!
Slave Ed
I like the idea of using dildos, then pegging then getting fucked. This is a great series. I identify with Brian. Hot stuff!
What has become of your great storytelling? You used to have all these great stories that actually did just that, told a story. Now you constantly put out one and two page stroke tales like most others here. I guess we should be thankful that at least you spell correctly and make complete sentences. You used to be one of the few who stood out. Whatever happened to stories like Bedding the Babysitter, Deconstructing Professor, Pet Mommy, Catching Mommy, and What Mom Knows? Classics one and all. I hope you find your way back to writing erotic stories, not quick spankers. Some of us can last a little longer than what a spankfest offers.
I think option 2 can come once he no longer feels like a stud jock
Start with option 1 and transition to option 2 ( sorry couldn't resist the pun). He could end up as Eugene's sissy wife. After all sissy hypnosis is all about the sissy being as girly as possible and a Sissy's who purpose in life is to serve a master or mistress. .A Sissy drivers her pleasure from giving pleasure to her owner (s). A sissy can serve a man or woman equally as long as it is understood what a sissy purpose is. Thats the real point of sissy hypnosis. To train a straight man to love being dressed in the sexiest girly cothes and sexually serve her man.
Great series can't believe how turned on I was, definitely want to see Brian pegged!
From the moment that you posted the first part of this series I've been hooked. So I always enjoy it when a new chapter is posted. Though with how short this chapter was it felt more like a teaser until you can finish a proper chapter. That being said it was still a great chapter and I am definitely looking forward to rereading the series.
I personally believe you should start with option 1 and have him learn how to get pegged and then have his first fuck be to a black man. But at the same time it would be nice to see him conditioned more to accept Rose as his Mistress. In addition, to having derive pleasure from pleasing her, sucking dick, and then taking it anally, until he cannot cum any other way. To help with this the two males would be Eugine and a black man that Rose knows. Then once he has reached this point Rose can begin training him to become a complete sissy that she can loan out. By sissy I don't mean a cross dresser where you know its a man but to live his life as female completely while being Mistress Rose submissive.
This is what I would like to see but either way I am looking forward to the continuation of this series.
Option 1 and 2 pls first she teaches him to take it in the ass then she feminizes him
He needs to be in a cheerleader uniform for a bunch of Eugene's friends at some kinda club meeting.
A variation of Option 2. I would love to read about more oral encounters with Eugene, possibly one in which they are both naked so Eugene could point out the physical differences between the masculine appearing Brian and himself, while emphasizing Brian's total addiction to sucking his cock. Making Brian grovel and beg for the privilege of sucking of Eugene would be a great turn on. Maybe Brian could be dragged down to a point where Rose can abandon him and completely turn him over to Eugene for his sexual pleasure.
Option 1: He is trained to be pegged in the ass... which will, in a future part... lead to him getting fucked in the ass by real cocks.
Option 2: He is slowly trained to dress like a girl until he is completely feminized.
.....none of the above. Keep him as a cock sucker. The story is much better that way.
Please option 2 with anal training as well. Maybe she starts him on hormones secretly? This would be awesome.
can it be both? would love to have him learn to love anal the same way he learned to love cock, and the only way to get them as much as he needs is to be fem as possible. also having him outed more and more is super hot.
I like Brian as a jock that is only secretly a Sissy, clothing could kinda blow that.
Mix in his dominant personality as the story progresses. His own sissy perhaps?
Definitely think the first option makes sense for the story. He's going from straight jock stud to cocksucking fag. Getting him to dress as a girl just wouldn't make sense for his character (not yet anyway) - maybe getting him to wear panties under his clothes could be doable.
These have been very hot so far so whatever you decide will continue to be so I am sure.That said I would go with option 1 and eventually work in option 2.Thanks for your stories
Option 1 would be better transition for the story cuz he already accepted his mouth as a cum deposit so his ass should be next
I think both would be good with him as a slut to Eugene and Rose. Eventually Eugene surprisez us all and becomes a master to all...including to a shocked Rose!
I think both options together would really be cool!! And maybe include a firehouse!! LOL!!
Mix of options 1 and 2, please! :)
Also, he's getting so obsessed with big cock, I'd love him to be trained to feel inferior because of his smaller cock size, to feel it's useless, so he can't cum without a cock in his mouth or ass.
Option 2....hopefully he is a Quarterback on the football team. He needs act as Eugene's new girlfriend......where a cheerleading outfit..... then wear Rose's black nightie. ...lol. Then Option 1....work it in slow.
Somewhat with anon on this, with mix of options 1 & 2. Like to see some loving bondage and submission in there too - Domme / sub wise, with the loving-trust that entails.
Option 1 follows the progression of the story better. Later Brian can be made to wear one or combination of panties, pantyhose, garter with stockings and/or bra if the guy he is sucking/getting fucked by wants to further control/humiliate him. However, Brian should not be outed dressed as a girl.
Please feminize the hell out of him, preferably make him resist it first as expected.
Option 1 makes the most sense for the story at this moment in time, in my opinion.
I think that Option 2 would come progressively after Option 1 though. He would enjoy taking it from her, then through whatever means he ends up getting the real thing and enjoys that as well. After this submission Option 2 would come into play solidifying all of his training and bringing it all together.
I could also see an Option 3 after Option 1 where he ends up in an equal relationship with Rose. He opens himself up emotionally and sexually becoming Roses perfect man, she accepts him completely and he does the same for her. Together they spend the rest of their lives in an equal loving relationship engaging in endless wonderfully depraved debauchery.
It's obvious where this is going to go he will become completely feminized but he needs to have the experience first of pegging strap on and sodomy training before he is feminized, heck the way it's going he might become one of the jock cheerleader chicks shake his ass with pom poms doing the football games
I prefer option 1: On the one hand it will show Brian all aspects of his physically sexuality, on the other hand i personally like that kind of story more than stories about "just" feminization.
having read the comments i would agree with most, option one leading to option two. although the thought of Brian in a cheer leader outfit getting drilled by a couple people besides getting pegged by Rose, would be so cool.
kisses
I think Rose should decide that not only should he be permanently feminized but he should be kept permanently locked in chastity and I mean permantlty. Rose should decide that he isn't allowed to fuck other girls or anyone else at all. His chastity device should be built in a manner that trains him to be unable to even have an erection. Rose should bring him to a painful understanding that he will never penetrate anyone ever again and should make him resign to trying to come through anal sex or through urethral sounding or rarely rewarded with a high powered vibrator against the case of his Chastity cage. Rose should also reveal that her interest in him is actually very limited and that he only got her attention is part of a calculated plan to eliminate her brothers annoying bully. He should also be outed at school not only as homosexual but as someone wearing a chastity cage permanently. His father should be so disgusted with his transgendered son that he subjected to humiliating beating and raping before kicking him out of the house forgiving him to one of his truck driver friends to keep out of his sight.
In chapter 2 as Rose is taking him into the adult store to the gloryhole this happens:
"Marry me," I joked.
"Play your cards right and one day you'll be my bride," she quipped
And that is exactly what she ought to do to him. That could turn out to be a happy, healthy, balanced marriage with him as the cock-sucking, crossdressing, closet sissy or they could be happy and healthy with him as her outright pet or maybe she feminizes and cuckolds him, sharing him with her big dicked boyfriends.
Any way that goes would be HOT. Please do finish this story with at least a lead in to the opening scene of chapter one. I'd love it if the revelation of who's fucking him is somewhat shocking...
He goes to the NFL and becomes a feminized cock sucker. Sucking the entire team and some. Others. Wear French maid outfit at NFL parties. Eugene is his manager.
Mark Parish
baroqueofisis@icloud.com
Honestly I'd say do both. Have him be feminised and trained to be fucked in the ass, unless it'll be too hard. In which case, I suggest one then the other.
Go the pegging route. My wife has started pegging me after years of playing with my ass. Now I have a 9 inch by 2.5 inch strap on plunging in and out of my "pussy" as she calls me her slut and whore. Makes me say "please fuck my pussy" before she starts.
I say go for the option 1, then once the craving gets to be too much, you go for the number 2.
I definitely think the crossdressing option would lead perfectly into the pegging one
I definitely say do both simultaneously. Eugene can start the feminizing, making him wear panties and stockings/garter belt, high heels, as a further domination, humiliation of the jock, while Rose can start pegging on her own.
Only question is who's gonna break his cherry first? Eugene or one of Rose's black friends? I'd say Eugene goes first, but then later Brian get's gang banged by a bunch of black guys setup by Rose.