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Five Year Anniversary of becoming a Cuckold Sissy Husband

Rating: 19
cuckoldjeff112

Member

Posts: 26 Pictures: 3 
#1 Posted: 26 Oct 2007 02:22
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These were some of the first humiliating pics of my wife dressing me up for a Halloween party five years ago. I had crossdressed before, but not enough to go out in public. I got a lot of stares from our friends both male and female. My wife enjoyed saying I was a naughty slut and I would love to get down on my knees for any takers. Everyone had a good laugh at my expense. This was just the first step in becoming a Sissy Husband.

I'll have more pics to come!
First Pic
First Pic
Second Pic
Second Pic
cuckoldjeff112

Member

Posts: 26 Pictures: 3 
#2 Posted: 26 Oct 2007 03:00
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I got my first "cock" to play with after the Halloween party. Sandie took me to an adult bookstore. She helped me pick out a nice collar, dildo, and male blow-up doll. She loved telling the woman behind the counter how I had a small dick and that we were going to try and have me be a girl for a while. These are some pics of me and what became my lover as she started to see real men.
Blowmansuck
Blowmansuck
Blowmandoggie
Blowmandoggie
cuckoldjeff112

Member

Posts: 26 Pictures: 3 
#3 Posted: 26 Oct 2007 03:06 · Edited by: cuckoldjeff112
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Here are two more with my blow up man.
onlyway2getoff
onlyway2getoff
learningtotake1
learningtotake1
jackie_rose68

Member

Posts: 2
#4 Posted: 26 Oct 2007 03:53
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You look beautiful in these pictures, do you have more?
Jackie
Jackie Rose
Suzi_sheffield

Member

Posts: 18
#5 Posted: 26 Oct 2007 12:19
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These are great
Please tell us more.
JHENCOLLANT

Member

Posts: 682
#6 Posted: 26 Oct 2007 15:27
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where is your woman

J'adore porter des sous vetement feminin ( bas, collant, string ) et je recherhce une vraie prise en main en suivi ct de versailles 78 ou en rgion parisienne
cuckoldjeff112

Member

Posts: 26 Pictures: 3 
#7 Posted: 27 Oct 2007 02:15
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I sort of became my wife's toy to amuse her. She liked seeing me dressed up and she loved to torment and humiliate me. She liked, well likes to gag me and then humiliate or torment me. The blow up doll was replaced and a larger dildo started to be used on my ass. I would sometimes get to watch her be fucked by her lovers. Sometimes I wouldn't. Sometimes she would do like in the picture and blindfold me and make me fuck myself on a dildo while I heard her get fucked by a real man. I was their own live small dicked, cuckold, sissy porno to watch and laugh at as they fucked.
toy
toy
live sissy porno
live sissy porno
SethPlate

Member

Posts: 382 Pictures: 1 
#8 Posted: 27 Oct 2007 11:40
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Great pics Jeff hope to see more
Licks And kisses
SethPlate

Member

Posts: 382 Pictures: 1 
#9 Posted: 27 Oct 2007 11:46
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cuckoldjeff112
Hey CJ
I would love to take the place of that doll the next to last pic is my Fav. you look hot and willing and ready for a good roll,
where you from?
Licks And kisses
cuckoldjeff112

Member

Posts: 26 Pictures: 3 
#10 Posted: 27 Oct 2007 14:34
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We're outside Chattanooga, Tennessee. My wife found a site about feminized husbands and loved seeing the men as maids. So, I became her maid to do domestic duties and serve her and her lovers takes. About this time the rest of my male boxers went in the trash and were completely replaced with lacy, frilly, and satin panties. I shaved what little hair I had off my body. My wife enjoyed spending my money on clothes for me as I started to dress more and more as a woman at home.
Long Legged Maid
Long Legged Maid
Blonde in Red
Blonde in Red
cuckoldjeff112

Member

Posts: 26 Pictures: 3 
#11 Posted: 27 Oct 2007 15:12
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I surprisingly took to my role. I guess it was a way to diminish some of the offense. I tried/try to be as good as a Sissy as I can be now. She still finds ways to humiliate and torment me though.
Dress gets me Noticed by her Lovers
Dress gets me Noticed by her Lovers
My Devious Wife
My Devious Wife
rubberist

Member


Posts: 129
#12 Posted: 27 Oct 2007 17:04
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Absolutely lovely pics!! I envy you.. You look stunning especially with your blowup man..
Rubber loving submissive crossdresser for women and men
peeweepp

Member

Posts: 1
#13 Posted: 27 Oct 2007 20:00
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Awsome!
cuckoldjeff112

Member

Posts: 26 Pictures: 3 
#14 Posted: 28 Oct 2007 05:59
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Oh yes we are. We now have seperate bedrooms. I get sex twice a year... on my birthday and our anniversary. Otherwise, I help bathe her and get her ready for her dates. I've helped her pick out a few guys on the internet. She loved having me type and instant message them questions about their cocks... if they don't mind me, her sissy husband watching. She loves having me tell them they can cum in any holes. I'll even eat the cum out of her holes or off her body. She enjoyed one time watching me be with one of her big lovers while she was on her period, but that's about it besides cleaning them up in between sexual romps. She laughs and says the guys are all hers to play with not me, her sissy husband.
All Fours on the bed
All Fours on the bed
Satin and Leather
Satin and Leather
cuckoldjeff112

Member

Posts: 26 Pictures: 3 
#15 Posted: 13 Nov 2007 14:30
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Sandie let me go with her to the hotel where she was meeting two guys. She tied me to the other bed, so I could listen and at times watch her get her pussy and ass fucked. She really loved getting fucked standing over the edge of my bed, so I could see and feel the cum on her face drip on my own face and watch her tits sway back and forth. She and her lovers laughed at my tiny cock and made me jackoff.
All tied up
All tied up
Jerking my little cock
Jerking my little cock
bich_gurl

Member

Posts: 2
#16 Posted: 19 Nov 2007 20:29
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so whats this website that your wife found? would love to check it out.
slutabob

Member

Posts: 36
#17 Posted: 26 Nov 2007 02:18
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I'm in North GA, I don't mind if you watch me fuck your wife. I get off on feminized sissy's watching. Heck I might let you lick your wife off my pole.
draclif69

Member



Posts: 3134 Pictures: 31 
#18 Posted: 26 Nov 2007 02:27
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They were right to treat you that way cuckoldjeff. Your small penis is more feminine than masculine and your type of "boy" is to be subjecated by their types, alpha males and females.
derra

Member

Posts: 19
#19 Posted: 7 Dec 2007 09:18
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I have been on mones again for a few months progynon depot spiro and depo, and suddenly I was on my way to more curves and bigger boobs ! and there is no mistaking the b-cup melons capped by , milky-looking nipples. the hormones gave me titties like these, but my male equipment is getting correspondingly smaller, in fact no bigger than a long clitty ! I am feminized siss, who has been turned into an abject, feminized slave for life !

I constantly play with my developing breast, I still work as a boy and I have been working at concealing them as much as possible, but lately I it has been a loosing battle. My body is waxed so to not show unsightly hairs. My eyebrows were tweezed within My ears were pierced I am Very sexy looking and a total slut when it comes to sex. I'm a T. girl who loves to be with those who appreciate T. girls.. especially other T. girls, but also men, and women, and couples.. open minded and uninhibited.. I love giving guys a good time. and will take and use haves.! so a guy really gets what. he wants. I am submissive so I need dominant guys I have allowed myself to be changed from a man into a totally submissive feminized sissy. I love to dress up like a real sexy slut, like a whore, because that's what I am, what I need to be, a cum takeing whore. All the better to attract more of the type of men I love, the type that love to use and debase me, love to fill the mouth and sissy-pussy of a little tranny slut like me. I just love to suck and fuck so that I could take down gallons,and massage in loads of lovely jism in to every square inch my little sissy body.
dderra feminized sissy
dderra feminized sissy
derra feminized sissy breasts
derra feminized sissy breasts
SethPlate

Member

Posts: 382 Pictures: 1 
#20 Posted: 11 Feb 2008 23:08
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cuckoldjeff112
Hi CJ
I was wondering if your wife ever lets you come out and play?
Licks And kisses
joguy

Member

Posts: 1444
#21 Posted: 2 Apr 2008 21:49
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your wife has made you into a hot fem slut cuckjeff!
joguy
name

Member

Posts: 1304
#22 Posted: 2 May 2008 09:46
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cuckoldjeff112
MrsBlackBlowupDoll

Member

Posts: 1201
#23 Posted: 14 Nov 2008 23:29
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CuckoldJeff112,

Your situation seems similar to mine, except that rather than starting with a blow-up doll, my wife finished me there. The only orgasms I get now are with it.
drdneast

Member

Posts: 1311
#24 Posted: 15 Nov 2008 02:03
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You look so sexy. I wish I could look as femmy as you. Would love to play with you in frfont of your wife.
joguy

Member

Posts: 1444
#25 Posted: 25 Nov 2011 14:31
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jeff is a hot sissy!
joguy
Manu

Member

Posts: 191
#26 Posted: 13 Dec 2011 10:53
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A BEAUTIFUL SISSY HUSBAND on an outing with her boyfriend.


suntzuson

Member

Posts: 220 Pictures: 3 
#27 Posted: 23 Dec 2011 03:47
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Manu
what an adorable sissy....certain she made her mistress very proud and the bf very happy!
houseslvsissy

Member

Posts: 5929
#28 Posted: 17 Mar 2013 21:58
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I wonder if Cuckold Jeff recently celebrated her 10 year anniversary?
chattanooga69

Member


Posts: 1229
#29 Posted: 17 Mar 2013 22:27
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mmm me too H.S.S its sad sometimes to see a pretty girl like her and than they just fade off would luv to know what and whom she is with today xx
houseslvsissy

Member

Posts: 5929
#30 Posted: 17 Mar 2013 23:14 · Edited by: houseslvsissy 
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chattanooga69:
mmm me too H.S.S its sad sometimes to see a pretty girl like her and than they just fade off would luv to know what and whom she is with today xx

I really do wonder. She is a very attractive sissy. It ends so bad for some, like Teresa. (I consider divorce and \or separation ending bad). Others .... like us ....seem to find a way to stay together.
Rating: 19, 5 votes.
Sissy and Chastity Forum CuckoldPlace.com / Sissy and Chastity Forum /
Five Year Anniversary of becoming a Cuckold Sissy Husband
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