A Tale of Two Sissies

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I meet cdcindy and we girls go man shopping.
5.2k words
4.49
14.7k
27

Part 1 of the 2 part series

Updated 06/12/2023
Created 12/22/2022
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eviltwin52
eviltwin52
1,707 Followers

This is a story of two gentle bois meeting through their respective spouses. Be fore-warned all you "Karens" who live to criticize others while accomplishing nothing yourselves. There is cuckolding and forced feminization included. You have my permission to MOVE THE FUCK ON. Those of you who like this genre, I hope this is to your liking.

You could say it was bound to happen. When an alleged man allows another man to fuck his wife can he really be considered a man?

My wife Cindy had tired of my efforts to please her sexually. "Except for your mouth, johnnie, you have nothing to offer in the way of sex."

Her constant berating me left me wondering what I could do to please her. When I considered allowing her to have sex with another man, I became aroused.

The thought I seeing his cock enter into what was once my domain excited me. I'd find out later that my arousal stemmed from the thought of that cock. But by then, it would be too late to change my destiny.

I broached the subject of Cin taking a lover with her. My proposal was for her to choose or have me select my surrogate. She was immediately and immensely excited by the idea that I would allow another man to take my place in my bed.

We thought about it, talked about it, and it was decided that I should be the one to convince the man of her choosing that it would be with my blessing that he fuck my wife.

Being completely truthful, the thought of me approaching a strange man and asking him to have sex with Cindy was humiliating. I would learn to love humiliation.

Cindy had a surprise for me. Instead of taking a chance on some stranger, she opted for my friend of many years, Tom.

Cindy had met Tom shortly after she and I began dating. Tom was the best man at our marriage, and she now confessed that she felt his much bigger cock when he danced a slow number at our reception.

"You know Tom so it should be easy for you to convince him that you're fine with him and me."

"But he's my friend and he'll think less of me."

"Oh johnnie, poor stupid johnnie, he couldn't think less of you."

It was then that my wife also confessed that Tom had already fucked her once. When I asked for the details, Cindy ordered me out of my clothes. "I know you'll want to beat your tiny dick and I want to watch while I tell you how Tom seduced me right here in front of all your friends."

What can I say? there's a little pervert in me. I quickly stripped and sat on the floor in front of my fully clothed wife listening and stroking as she regaled me with the way Tom had "playfully", her word, hiked her skirt up and pulled her panties down while 4 of my buds and their women watched.

"Remember when Tom sent you for more beer that night? He'd been coping feels and cornering me all evening. When he put my hand on his big cock, johnnie, I knew I had to give him what he wanted."

"And what you wanted," I countered.

"What I needed you mean. Anyway, you left and even before we heard your car start Tom began to treat me like I'm his personal slut. When he pulled my skirt all the way up, he told me to hold there."

"What's a girl to do when a real man decides she is his? Tom led me around the room asking everyone if they wanted to see more of me. Well, you can imagine they all wanted to see more. To demonstrate what a man he is, Tom had me stand barefoot on our coffee table. Mind you, johnnie, I was still holding my skirt up."

"I was wearing my red panties, the one you like so much. Tom pulled them down and helped me step out of them to the applause of your friends, johnnie, your friends. They all saw my pussy and ass."

"Oh, God Cin. What happened next? Did he fuck you in front of everyone?"

"No. First, he twirled my panties around like a trophy and asked what he should do with them. Most everyone said he should keep them. But Tom made them all laugh when he said he should put them on you. You, johnnie. All your friends wanted to see him put you in panties when you got back."

I almost came hearing my friends wanted Tom to put me on panties while they watched.

The ladies all wanted Tom to fuck me right there. "Bend the bitch over and fuck her, Tom," they clamored.

"But Tom is a gentleman if nothing else. He just smiled and took me down from the table and led me into the guest bathroom. He shut the door and had me sit on the commode. I watched him open his pants and pull his hard cock out."

"Wow," was all I could say.

"He let me suck it for him before he stood me up. Then he had me leaning against the sink. I watched in the mirror as Tom fucked me from behind. johnnie, it was what every woman should experience. A real man claiming her pussy and using it for his pleasure."

"God Cindy. At least no one else was watching."

"Tom did open the door for those curious friends of yours to watch. He would slow down and stop which made me beg him to keep fucking me. He told me he was going to fuck me whenever he wanted to the cheers of all your friends. It was so hot."

"Did, did Tom um, cum in you?"

"He did. He filled me with a tremendous load. You probably don't remember but when everyone was gone, and I sat on your face. I fed you Tom's sperm. You loved it. Tom told me to do that. He knew you'd like it."

Hearing that made me cum. I groaned and jerked had spasmed through one of my best cums ever.

"So, now you know it won't take much convincing for you to talk Tom into fucking me again."

"Do you want me to call him and ask him now?"

"No, johnnie. I want you to invite him over and ask him in front of me."

With my arousal satiated, I tried to man up. But as usual, Cin beat me down. Not physically but mentally. I called Tom like she wanted.

"So, what's the big deal, johnnie?"

"Um, I have to wait until Cindy joins us, Tom. She insisted on being present. She's changing and will be here in a minute."

I began removing my clothes much to Tom's surprise. What the fuck, dude?"

"Uh, it's like this, Cin told me to be naked when I tell you why I called you."

I knew what Cindy wanted by having me naked. My wife wanted Tom to see my 5" quarter sized circumference boner I'd get from the humiliation of asking him to fuck her.

Cindy appeared in her floor length pink robe. What she had on under it was anyone's guess. My guess was, not too much.

"I see we're ready," she smiled and walked up to Tom. I watched them kissing, sharing tongue as Tom felt free to run his hand over her generous bottom.

When they stopped kissing and faced me, Cindy said it would be respectful of me to be on my knees when I asked Tom what I wanted from him.

Like we discussed, I knelt; my legs spread so my boner would be totally exposed. "Tom, Cindy told me what happened at our party when you sent me out for more beer," I began. "She told me how you made her feel more like a woman than I ever have."

Tom smiled at me and I saw Cin reach for his cock, feeling him through his trousers. "Go on," Tom urged.

"It's clear to Cindy that you're more of a man than I'll ever be and for that reason, I'm asking you to take my place in her sex life."

"Wait," Tom grinned. "Are you asking me to fuck your wife?"

"Yeah," I answered. The humiliation was nearly overpowering.

"Then ask me that, just that way."

If I had just touched my dick, I would have cum. "Tom, please fuck Cindy, my wife," I managed to croak.

"Yeah, I hear you but how do I know you're sincere? You might back slide one day and get all bitchy on us."

I was at a loss for how to show him my sincerity and said nothing as I tried to think of a way to prove what I was saying.

Depending on how you look at it, Cindy came up with was a suitable solution. To them anyway, it was a solution. To me, it was a life altering event.

I stayed on my knees and watched my wife open Tom's trousers and pull out his beautiful big cock. She told hold of it and led Tom over to where I was kneeling. Bringing his cock to my lips, Cindy smiled down at me.

The she looked at Tom and told him to go along with this. Tom just shrugged.

"johnnie, I think you could convince Tom by sealing the deal with a kiss to his cock."

With his cock right there, I leaned forward and placed a quick tentative kiss on the large, flared head.

"You can do better than that, johnnie," Tom scolded me.

I didn't yet know that I would come to love what I did next. I kissed his cock head again, taking it into my mouth and giving it a tongue bath.

When something feels right, it just feels right. You never know what it might be. That night, pledging my sincerity, I found that having a large cock in my mouth just felt right.

"This mother fucker sucks cock better than you, Cindy," Tom praised me.

Cindy didn't take it as well as I did. "Then maybe johnnie should suck your cock instead of me."

"I agree," Tom said.

Both Tom and Cindy watched me for the next few minutes as I explored Tom's cock with my tongue and hands. To my credit, Tom seemed to have forgotten all about fucking my wife.

Until he didn't.

"How about showing me what you have under that robe baby," Tom suggested.

Cindy opened her robe to show Tom she was naked except for the red panties. "I'm wearing johnnie's favorites," she smirked looking at me. "Take me to bed, lover. I need that cock, my husband is sucking for me."

Tom became a regular visitor until he eventually moved in with us. He promised me he wouldn't try to take Cindy away from me. "Dude, that's why I think it's a good idea I move in here."

If I harbored any thoughts of two guys and a woman, those thoughts were dashed almost immediately. I quickly learned my place among the three of us. Tom was top rung along with Cindy. I was bottom rung.

Tom had decided to lay out my chores which he inspected and made me correct any flaws.

The more I obeyed him, the more dominant Tom became. In less than a year Tom had me shave my entire body but instructed me to leave the hair on my head grown long.

One night I was sucking his very manly cock when Cindy came into the room wearing only my favorite red panty.

By then, my hair was nearly shoulder length and I had it in a pony tail so as not to get in my way when pleasuring Tom.

You're wearing johnnie's favorite panties again. You do that to torment my cock sucker?"

"I wear them as a reminder that what's under them used to be his," Cin laughed. "Hey, you remember the first time we fucked? You told everyone that you might make johnnie wear them. What do you say. Is he ready to be a pantied husband?"

"Let's be nice about this, Cin," Tom said. "Let's give johnnie a choice."

"A choice between what," I asked with some trepidation.

"I'm tired of seeing your pathetic boner. johnnnie, which would you rather wear full-time; a chastity cage, if I can find one that small, or panties?"

"Please, Tom," I begged removing his cock from my mouth. "Don't make me choose that."

"Alright, johnnie. I won't make you choose. We'll leave it to fate or luck, which ever. Cindy, get me a quarter."

Cindy rose and got a quarter out of her purse and handed it to Tom.

"This is how we'll decide, johnnie. Heads you wear panties, tails you're caged."

I held my breath as Tom flipped the coin. I didn't know which I wanted to come up, heads or tails.

In less time than it takes a fly to find shit, I was pulling my red panties for the first time.

"She looks good in them," Tom teased.

It would be a while before I knew how I looked in panties but I loved the way they felt on my bottom and how they hugged my boner and balls.

Cindy laughed when she saw me rubbing my nylon covered butt. "She feels sexy, Tom. As I recall, johnnie's friends wanted to see him wearing panties. I think we should invite them all over to see what a cock sucker he's become. A panty wearing cock sucker at that."

A week later, the same 4 couples who witnessed Tom fucking my wife were back to see me in panties. I was made to wait on them, carrying a tray of snacks and making drinks.

There were smug comments and much fun made of my boners wetting the front of my panties. Someone asked if I wore them all the time. Just as soon as I finished saying I didn't wear them at work, Tom corrected me. "She will now," he said piling another layer of humiliation on me.

Before that night was over, all my friends saw me suck Tom's cock until he fed me a load of his savory sperm. Although he offered, no one else took him up on his generous offer to stuck their cocks in my mouth. But I was treated to a wedgie that bared my bottom almost completely.

It was all so humiliating but not as much as when Tom had me masturbate in front of them. Thankful for the release as I was, it was so belittling. Knowing that there would be no coming back from this, I'd be a cock sucking, panty wearing, jack off forever in the eyes of my friends.

When everyone knows you happily suck cocks and wearing panties, why try to be anything different? That was what Tom thought anyway. After he easily turned me out to my friends, Tom began to feminize me in earnest.

I was not enthusiastic at first. Tom made it abundantly clear that this was what was best for me. I came to believe Tom was right when I first begged him not to make me wear women's clothing. He told me that I was more woman than male and besides that, he said, "Cock suckers are followers, not leaders." My belief in Tom was not because I didn't feel that all cock suckers should follow. No. The one glaring fact that I had to accept was, I felt sexy and pretty in panties. So, if Tom was right about that.... you know the rest.

I soon ad an array of women's lounge wear and a clutch filled with make-up in less than two months. Tom would have me in panties, a garter belt, and hose as I went about my chores and I soon came to love the new sexier me.

Lounge wear evolved into sports wear; tiny shorts, a sports bra, pink sneakers, and camesole tops. I wore those to tend to the flower bed Cin had me plant for her. Soon I was running errands in my femme clothes.

More than once a man would grab my bottom in the grocery store which had the effect of making me feel desired.

I was wearing capris pants and T-tops to work with appropriate open toed shoes that showed off my painted toe nails that matched my fingers. Carrying a purse with my hair brushed out at my shoulders and lips stick along with eye liner and mascara, I was the modern girl. And that what I was wearing when that strange man held my bottom.

Later that evening, I was on my knees making love to Tom's cock and told him about what happened at the grocery store.

"Baby girl," he said holding my chin so I would look at him. "Didn't I say you'd make a better woman than a man?"

I began, with Tom's permission of course, to correspond with those like me on the internet. One sissy was cindy. She wanted so badly to come out to her wife she was nearly frantic. But she was afraid her wife would not understand nor accept the fact that cindy preferred cocks to pussy, men rather than women.

My Cindy, who was growing disgusted with my new life decided to investigate those with whom I was emailing. She did so without my knowledge. Pretending to be me, she asked cindy for her phone number and wrote that I/she would call when cindy's wife wasn't home. Instead, and unbeknownst to me, she made sure cindy's wife was home when she contacted her.

So it happened that one Saturday night Cindy and Tom ushered me out of the house naked except for a garter belt and hose, and my 4" heels. Placing me in the back seat, I rode like that for over 4 hours. "We've got a surprise for you, jennifer," Tom said giving me a name more suitable for what I've become.

In doing so, Tom took away from me my last shred of manhood.

He drove us to a city that I'd never been to before. It was getting daylight so Cindy tossed back a blanket. "Cover yourself, slut."

Tom soon pulled up to a nice apartment building. "Is this the place, Cin?"

My wife checked the note she had. "We're here, Tom. Let me call up."

"Wait," I cried out. "Where are we?"

"Hayward. We're here to see a friend of yours."

My heart was beating fast. "Who do I know in Hayward?" I wondered.

Cin got out of the car so I couldn't hear what she was saying. After a short minute, she smiled at me. Wrap yourself in the blanket and come with us."

Tom retrieved a suitcase from the trunk and walked with Cindy. I trailed after them.

It was embarrassing because that building had a doorman who gave me a funny look.

Cindy spoke to the doorman privately. He looked at me and grinned. "Apartment 14. Right off the elevator, 4 down on your left. I'll ring them and let them know you're on your way up. She told me she was expecting you."

I started asking questions but Tom silenced me. "Now jennifer, don't make me spank you in front of your new friend."

Cindy knocked while Tom and I stood behind her. The door was opened by a beautiful woman near about Cindy's age. "Welcome. How was your drive?" she asked leading us into the spacious apartment.

My wife introduced Tom to Linda but excluded me.

"Long drive," Tom said. "Typical California traffic up 101 to the San Mateo bridge."

"Believe me," she smiled. "I know. And who is this beautiful creature?" She smiled pointing to me.

"That was my husband, johnnie. Now she's jennifer the sissy."

Linda hugged Cindy. "I'm glad to know I'm not the only one saddled with a fucking homo. You can come now, cindy."

"Please excuse any confusion. My cross dressing husband named herself cindy too. She didn't think I knew of her proclivities with the same sex. I learned of her perversion only last month. Now she needs almost as much closet space for her outfits as I do. How on earth did she think I wouldn't find out, God only knows."

A door opened slowly and out came a pretty lady. I knew from her Adam's apple that she was like me. She was wearing hip hugging tight white pants which accentuated her fabulous bottom. I could see the little bulge in front that screamed "tiny dick aboard".

My dick grew instantly erect under the protective cover of the blanket. But that didn't last long. "May I?" Tom asked.

"Please do."

Tom whipped the blanket from me leaving me exposed in my garter belt, hose and shoes. My stiffy all but "shouted look at me".

Tom, Cindy and Linda went to sit. "You girls get acquainted now that you've met in person," Linda instructed us.

"Take your suit case, jennie. You and Cindy are going out tonight."

"Where," cindy asked in a quiet voice.

"Club Eros, in the city where you two fairies can meet like minded faggots like you," Linda spat. "Now go to your room and take the other faggot with you."

I looked to Cindy and Tom for guidance. Both nodded.

cindy was resplendent in her white pants, purple fishnet top, and purple pumps on her small feet.

Once in her room, cindy closed the door. Turning to me she asked if I preferred johnnie or jennifer. "I'm jennifer now, I guess."

"I was hoping you'd say that jennifer." She came to me and we hugged. She hadn't mentioned yet my lack of clothing. Instead, she took my hand and placed on her bump in front.

I gave her a gentle squeeze as our lips met for the first time. I moaned into her mouth. It had been so long that I'd actually been intimate with someone. Sucking Tom's cock isn't exactly together time. It felt wonderful to be held and kissed.

It seemed to me that cindy was a bit timid with her wife in the same room. But once alone with me, she showed me another side. More confident, cindy knew how to deal with a sissy like me.

cindy reached down and held my straining boner. "Cute, baby girl. Not enough to suck but cute anyway."

"You do that too?" I asked hoping cindy was like me.

"If you mean sucking cocks sweet heart, I've been a cock sucking faggot on the down low for a couple years now."

eviltwin52
eviltwin52
1,707 Followers
12