Sissy Acts Out Fantasy

My wife has slowly stopped having sex with me. After 20 years of marriage this is more about her decreasing desire than fulfilling my fantasy.

It is true that I am a small dicked sissy boy. For years I thought I was normal to above normal. All the girls i dated were very nice and always said I had a nice cock, or it was a good fit or something kind like that. They also said "is it in, yet?" after I had already started fucking. And "are you done?". Plus I was never able to fuck long and hard. When I tried my cock would always slip out, so I was always a slow and soft kind of fuck.

I was also obsessed with eating pussy. I almost preferred it to fucking. I was very passive in bed, never asked anything of my girlfriends.

In my day to day life I am also rather passive and sensitive. I don't like action films, I prefer romantic comedies. I'd rather go shopping with a girlfriend than go out takeing with the guys.

When I look back on my life I realize I was cuckold many times. I never realized that the cuckolding was what I liked most in those relationships. I focused too much on the offense on jealousy. Today I would do things differently.

Back to the present. We rarely have sex now, once or twice a year. I get a handjob maybe once a month, less and less all the time. The less sex I have more my cuckold fantasy grow. Occasionally I try to live out some of my fantasies.

Last week I wore my bra, panties and stockings and went to the local adult bookstore. They have "fantasy booths" where you can go and talk to a girl through a glass partition. Most guys get a strip and masturbation show. As a small dicked sissy I know that no girl would want to do that kind of a show for me.

I went and told her about my wife's lack of interest and how I was to small to satisfy her. I created a a big dicked, Black boss for my wife and said they were on an out of town trip together.

The booth girl told me that little dicked pantie boys need to accept that their wives need real men. She showed me a picture on her cell phone of her Black boy friend's huge cock. She asked if I sucked my wife's lovers cocks. Yes. Did I like? No. I like cleaning her cunt after they fuck her. Do her boy friends fuck me in the ass. NO! She had me fuck my ass with my fingers. When the time was up she talked me into getting a butt plug. She helped me pick it out and let the clerk know that I would be wearing it because I had a little dicklette.

I went to the video booths and insert the plug. I went home wearing it, but came back to the store about an hour later. I had to receive more offense from the booth girl. When I got there she was talking to some friends, a guy and girl. She told me to kneel on the floor and wait. Her friends smirked, and other shoppers cast glances at me kneeling in the store. After a few minutes she asked if I was still wearing the butt plug. Yes I said as I caught her friends looking at me with raised eyebrows. First the guy left and said something snarky to me as he passed. Later the girl left laughing at me while looking me in the eye.

Finally I was able to get another fantasy show. She had me fuck myself with the plug and this time I came in my panties.

True.

Let me know if you would like to here more true stories of how I humiliate myself or of my past girlfriends cuckolding me.

Yes great story, what color were the bra and panties.

Thank you.

The bra and panties were pink. Great sissy color. I also have black and red sets. The pantyhose were cheap and a neutral color. The butt plug was black. I had to tell the clerk, "no, the black one."

The bra and panties I was wearing were from a thrift store. The plus is that they are cheaper there, and the thought that some hot woman was wearing these sexy undies while fucking her boyfriend before donating to the thrift. The clerk said "you'll look cute in these". Then quickly she added "just kidding". I ignored the second part and said "thank you, I like them" looking her in the eye before blushing and looking down. The pantyhose were bought uneventfully at a discount store.

I have bought undies at garage sales, which can be really hot. You get to look at the woman who original bought and wore them. It is also a much more permisteral transaction. I often get too scared and embarrassed and just leave them.

I've bought undies at sexy lingerie shops that cater to strippers and couples who want something steamier than Victoria's Secret. These are good because most often the clerks are sexy and willing to listen to my sissy cuckold fantasies, as long as I don't get graphic. I tell them "My wife doesn't want me wearing her bra and panties any more so I have to buy my own". They giggle and ask if I want thong or full back. They may ask if my wife likes me wearing undies. "Her boyfriend demands it" I will reply. These shops will also allow me to change into my purchases there, which is a big turn on.

The most exciting and humiliating purchase was from a mall department store in a mall. I told the clerk I wanted a size 36 B bra and matching panties. (To get your bra size measure around your chest just under your tiny titties. Unless you are real flabby you will be an A cup. But they don't stock many A cups so ask for B) She asked if they were for my wife. "No, they are for me. She makes me wear them." She gave me an approving look. What color? Don't you think I should wear pink. The lingerie dept was almost empty and she took lots of time helping me pick out 2 appropriate pairs. The whole thing was very professionally done, but extremely humiliating. She would not let me use the store changing room. The most humiliating moment was yet to come. As I left the store the security alarm went off. I immediately turned around and went back before security caught me. She had "forgotten" to remove the security tag.

I have not successfully bought undies again in a mall store. I always chicken out because they are too crowded. Or because there are teens shopping, and I don't want to subject kids to my perversions.

Where do other guys get their dainties.

You're very brave. I'm too big a sissy coward to do such a thing.

Sudycat what a story, i am not that brave either. I love the part at garage sale i would like too try that.

Thank you. Garage sales are great. But also the hardest I think. Often I will pick up a pair of panties at a garage sale, but then see some guy who is looking at the tools stare at me, and I put them back. Or some granny looking at china will give me a withering look. Or maybe I proudly march to the where the money is being taken, only to have her elderly ladyly, or youngren come out of the house, and back they go.

I went to one sale once where a very hot young lady was selling off her pre ladyhood clothes. There were lots of extremely sexy undies. No one else was shopping and she was anxious to make a sale. I let her know they were for me. She was telling me I should buy these, and I should buy those. Her bras were in a lot of different sizes because her breasts kept growing as she went through her pregnancy. She seemed to think that leaning over and giving me a good view of her now very full breasts was a good sale technique. She was right! I bought a few things including a pair of satin and lace black panties with a matching padded bra that I still wear. She charged me way more than they should have been at a garage sale. Like $5.00 an item instead or .50c. It was worth every Penny.

I am not a crossdresser. I don't wear dress or skirts and blouses. I don't try to pass. I don't even shave my body. I am just a small dicked sissyboy who needs to wear women's undies.

The fantasy booth women (see first story) wants me to wear heels next time. What do you think?

if she wants you to , you should do it!
joguy

sudsycat
Not to rain on the parade, Sudsy, but how about talking to your wife about some of your fantasies? It might blow on the embers of her sexual interest a little. Even if not, after 20 years of marriage she may be willing to accomodate you or even get some other non-sexual satisfaction out of working you over a bit.

Think about it. It is potentially more rewarding and definately less risky than making a habit out of the fantasy booth.

Good luck.
Pantalone, Wittol, oblate, abnegator, fellator, pathic, irrumatiophile,fop, epicene, cotquean, skivvy, thrall, and pilgarlic.

Thank you. You are right of course. I need to step up and talk to her. She knows I like to wear her undies, but has never encouraged me. Around her I have only worn them during sex play.

When we met my biggest fantasy was voyerism and exhinbitionism. She was great at accomandating my desires. We had sex in public a few times, and still go to places with public nudity. She would ask me why I wanted other men to see her. I never had an answer besides I enjoy it.

I'm jealous that you've grown as much as you have and I haven't. But, I do smile at reading how much pleasure it gives you.

I saw a movie a few days ago you may be interested - The Secretary. It's not exactly in line with your actual sissy fantasies but it's related because it's about a girl who goes through a self discovery. And, it's super hot watching her do it. Highly recommend it...I suspect you'll see a bit of yourself in it (if not pick up a few dressing tips - heh).

thank you for sharing this....i too have acquired a need to be humiliated...

https://www.cuckoldplace.com/12_18659_0.html

(this is the one you've already seen, but maybe others who see your stories will be interested too.)

it's amazing what you did....go to the girl that way...and you were very, very lucky that she responded to you the way she did...

although i've never wanted to be completely dressed as a girl...mainly because i'm too big to be pretty...i've long had a thing for panties...my wife knows that i get into her hamper and masturbate into her panties and little bras....usually she ignores it, but when i'm lucky she tells me it's pathetic and dirty and that i should be ashamed of myself...when i'm very, very lucky, she'll let me watch her get dressed for work...ignoring me except asking me if i've been getting into her panties again....telling me how dirty and shameful it is, but letting me masturbate while she talks to me that way....maybe she'll look over at me and ask me if i'm enjoying myself....that sort of thing....

what she doesn't know is that years ago, just after we were married, i used to dig through her things and find the prettiest laciest daintiest little panties, and put them on under my ragged, graduate student jeans....(i was thin and pretty for a boy back then)...i'd go downtown in my pretty little wife's dainty panties....and go from one x-rated video arcade to another....half disgusted, half high from sexual arousal as i watched pornography involving pretty asian women like my wife while desperate men talked to me through the glory holes....begging me to put my cock in them to suck....some of them noticing what i was watching...noticing my wedding band....talking to me...talking talking....are you married? to a pretty asian girl?...she doesn't let you fuck her? are those her pretty panties?....put your cock in the hole...pretend it's your pretty little wife sucking on it...it's okay....i won't hurt you....things like that....sometimes...if the images on the screen were just right, i'd do it....

other men would sometimes try a different strategy, that occasionally worked....they'd taunt me about the panties....they'd tell me to stop playing hard to get....they'd call me a pantyboy....a pussyboy...a fag....these were the men that i would sometimes let into my booth....if i was high with sexual arousal, and if just the right video was on...i'd let them handle me....or sometimes suck me....a couple of times i let the man rub his cock on my face and push it into my mouth....i must not be very good at giving head, though...i never made a man cum....at least not from my mouth....many have jerked off onto me, though....

my wife doesn't know about this....she'd leave me if she did....i stopped doing that several years ago when i didn't get that kind of attention anymore....

Thank you Dale. I also have stories a lot like that.

Like most men here I am straight but... I like watching a women enjoy a big cock. I have also worn panties, and sometimes bra, to the video booths. I've also let men in, but try to resist their advances. I do enjoy telling them that my wife's boyfriend makes me wear panties. I like telling them about her and her boyfriend. Of course it is all fantasy. I try to keep it to just talking, I am really not interested in having sex with strange men.

I met a guy who reminds me of your other story about the guy at the hotel bar. He asked me if I ever joined my wife and her lover.
"Sometimes they let me watch, and then I get to ear her pussy."
"Do you eat his cum out of her pussy?"
"Yes."
"Do you like eating his cum?"
"No, but I like giving her pleasure, what every it takes."
"Do you suck her boyfriends big black cock?"
"Sometimes they make me clean it with my mouth after he has fucked her. Or I will suck him hard again for her."

I've had this conversation with a few guys I have let into the both. This one guy was real aggressive and wanted me to suck his cock. Unlike a lot of trolls he seemed straight, didn't try to touch me. He just wanted his cock sucked and now. He also had a very big cock.

I was standing there in my bra and panties and he told me "Sucking cock is what you do. Now suck mine." I made him wear a condom, but I did suck him. It was as disgusting and repulsive as it was exciting and humiliating.

wow...it's amazing to find that someone else has had so many common experiences as me....for me, though, steering conversations in humiliating directions is really new for me....but there were several years...years ago now....when i would tease dirty old men...and the occasional young one...while simultaneously humiliating myself by wearing panties....i'd always resist too....at first i wouldn't let them touch me....then, eventually, i would....for some...sometimes...i'd eventually let them suck me....the couple of times i actually let a man put his cock in my mouth...i was so aroused....so high, really....it was like i couldn't stop myself....but i was stupid....i didn't make them wear condoms....it was unsafe and stupid....but there it is....

Sex is a dangerous thing. All the red flows out of your brain and into your dick.

I think you are braver than me. When I talk to strangers in video booths any thing goes. But to talk to a stranger in a bar is really laying it out there.

A few weeks back I went looking for some public offense.
Dressed in my cutest matching pink bra and panties (plus fishnets over panty hose and a shaper) I went to a local adult bookstore that has live private shows.
Often the women are too nice too humiliate me, Sin was not shy about laughing at my pathetic penis clad in pink panties.
She teased me for 15 minutes, giving me only flashes of her amazing breasts, and refusing to show me her pussy.
She laughed at me, told me I should be sucking cocks and should forget about any woman ever being interested in me.
Most of the woman want you to jerk off as fast as possible and leave, but she teased me for the whole 15 mintues.
She then had me wait in the lingerie section while she did a show with a real man.
While waiting a couple came in and started to shop for lingerie.
Finally Sin came back and teased me again before sending me home with my clitty straining my panties.


I wasn't done with my need for public offense.
I went to the discount department store to buy myself more girly undies.
I was dressed in matching black and white bra and panties.
The lingerie section was huge, but I could not find any matching bra and panties.
I did find a really nice black shaper.
I spent a long time shopping, many woman saw me trying to find a matching top or bottom, plus a few guys with their girlfriends.
Finally I took my shaper to the check out line and stood there until it was time for the clerk to smirk at my as paid and headed out the door.

In the car I slipped on my new shaper and headed back to see Sin.
She was far meaner to me than the night before.
She made me fuck my asshole with 3 fingers, I had never had more than one there and it hurt as urged me to go deeper and faster.
Then she spit in my face and made me leave it there, so when I left I had to walk through the store with her spit dripping from my face.

It was great and I can't wait to go back again.