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Annie's Room

Have you introduced a sexual partner to a new kink they never tried before?


I just introduced a virtual sex partner to pegging (and feminization!) The pegging was quite well received and I think the feminization is as well.
 
SweetAnnie40 said:
Have you introduced a sexual partner to a new kink they never tried before?


I just introduced a virtual sex partner to pegging (and feminization!) The pegging was quite well received and I think the feminization is as well.
Click to expand...


Sounds like fun to me! Welcome back, Annie.
 
Out of town hotel fun. I got hit on tonight. :)

https://forum.literotica.com/attachment.php?attachmentid=2119037&stc=1&d=1622013875
 
Annie, thanks so much for encouraging the breast forms, they feel great! I can barely keep my hands off of them. ;)






https://forum.literotica.com/attachment.php?attachmentid=2119092&stc=1&d=1622107049
 
Last edited:
Don't let me interrupt the sissy hijinx here in my room :rolleyes:

Submitted to Literotica a story I'd written a couple years ago and rediscovered. Inspired by some of the fantasies my husband shared with me and seeing if I could do service to the sissy's viewpoint. Thought I'd give you a first peek...


Bitcoin Bill -

I've been living the good life. I made a killing in digital currency and cashed out last year. I was only 30 years old and ready to enjoy the good life. I bought a Bugati supercar. I bought a Beverly Hills mansion from a former Oscar winner who needed the cash. I even bought a super hot girlfriend with a high libido.

Well, I didn't _buy_ the girlfriend but might as well have. I'll confess that I'm not some he-man stud. I'm well toned but slender for a guy and only 5'6". Daphne is 5'8" before putting on her heels. Still my money did the trick to get her excited and things were good for awhile. She was so eager to get married and have a social event wedding that she barely blinked at signing the pre-nup that would protect my fortune should things go south.

Which, of course, they eventually did. Money is great but it really doesn't help when I can't satisfy her in bed. It eventually became clear she was faking it. My cock is barely 5" when I'm really turned on and feeling her just laying there didn't help me get full size. She started jacking me off instead of intercourse and then getting back to her online shopping or planning our next publicity-seeking date night. That was kind of humiliating but I couldn't argue the point.

I don't know when I started suspecting she was being unfaithful but I eventually hired a PI named Eloise to see what Daphne was doing on her shopping trips. For a few weeks it all seemed innocent. Then I was given video of my wife coming out of a women's restroom clearly disheveled and followed after a few minutes by a studly guy with a soul patch still tucking his shirt back in. Highly suspicious but not good enough for court. I kept Eloise on the case until she finally brought back video of my wife naked on a hotel room bed being fucked royally by Mr. Soul Patch who did have a remarkable cock. She came like she never had with me. I watched that video a lot before deciding that I had to get a divorce. I was definitely mad but also kind of ashamed when I saw how much a real-sized cock gave her pleasure. My own boner while watching it wasn't helping. Let's just say I had a lot of mixed reactions watching those videos.

When I reached out to Eloise, I couldn't reach her. She stopped returning my calls. Her evidence was in the cloud but I found I wasn't able to access it any more. That was critical for my divorce case. I finally received an email from her claiming a new conflict of interest and that she would no longer be working for me. She even returned the fee I'd paid her. I considered suing her but didn't want to alert Daphne. So I set about to find another PI who could catch my wife fucking around on me.

So last week, Daphne promoted another splashy date night to keep our names in the papers. I went along with it, not wanting to tip my hand. She was very attentive and the papparazi filmed us with a couple A-list celebs so maybe the coverage wouldn't suck. When we got home, Daphne wanted to continue the party. I wasn't that interested, partly because of what I knew I was doing to her but also thinking of that guy with the big cock just made me feel so inadequate, I didn't want her to be seeing or touching me. But she was insistent and we kept drinking. I usually don't drink to excess but I went over the line that night and frankly barely remembered anything. I know we spent a few hours in the bedroom talking and fooling around. I was really talkative, much more than I ever am normally. But I was telling her everything she ever wanted to know. Just alcohol never did that to me. The rest was pretty hazy... at least until I woke up.

I was spread-eagle on the bed in the bondage gear we'd bought a couple months back for me to put Daphne in. She'd never agreed on what night we were going to try it so they had still been in their box. A quick check confirmed that she'd put it on right and I wouldn't be getting free without her. Each wrist had a leather cuff buckled and locked on it and the same for my ankles. The cuffs led to straps that were firmly anchored under the bed leaving me just a little play... enough to struggle and confirm that I had nowhere near the strength needed to force my way free.

Moving around also told me more about my situation. I wasn't naked but rather wearing her clothes... well, her lingerie and some dress. I couldn't see my feet because there were boobs in the way but I felt stockings and high heels on them. Felt like I had her bra on and she'd stuffed the cups before putting me in the dress. Or did I put the dress on? Why did I drink so much?

I took inventory and felt high heels, thigh high stockings, panties, a garter belt, the stuffed bra, and the tight dress. Yeah you can ask how I could recognize it all so easily but I'll let you wonder on that point. All will become clear soon enough. Looking around, she wasn't in our bedroom with me and the en suite bathroom was dark. Moving around had caused my body to react to my predicament. My cock was getting hard in the satiny panties.

I groaned. I must have told her about all this. When I was a teenager I got really into lingerie as a fetish but after college I told myself I was done with it. Sure, I masturbated thinking about it over the decade since but I'd never indulged. Clearly drunk me blabbed about it and now she knew all about my lingerie fetish... hopefully just the lingerie.

Laughter drifted up from downstairs. Daphne, another woman, and at least one man were down there. I froze. I couldn't let anyone see me like this! She wouldn't dare. She probably did all this to distract me from discovering her infidelity. I just had to play along until she let me out of the bondage. Then things were going to change.

Things got quiet downstairs and eventually I heard someone come up to the bedroom. It was Daphne carrying two cups of coffee. She was still wearing a bright red satin teddy and a sheer coverup.

"Ah, good, you're awake. You were so tired I figured you needed to sleep in." She sat in a chair, setting one cup on a side table and holding the other in her hands. Steam came off the top of the cup and I could smell the Colombian roast I preferred.

"Uh, yeah, if you undo these," I said calmly, moving my arms and legs. "I'd love to sit up and have some coffee." She smiled in a way that unnerved me.

"Not... quite... yet. I want to show you something first." She picked up the remote from beside the bed and turned on the big screen TV I'd had mounted so we could watch things in bed.

The screen began dark and there wasn't any sound. Then a door opened letting light into a room, into our bedroom. Daphne and I were swaying a bit as we came in, kissing, and teasing each other. In the video, Daphne turned on the light, gave a wink to the camera, and then returned her attentions to me.

"Let me just get to the good parts. You'll be able to watch the whole thing any time." As she fast-forwarded, I could see us getting down to our underwear and then sitting on the end of the bed, drinking and talking for a long time.

"Here, here we go..." The recording returned to normal speed and she turned up the volume as her recorded self stood up to face recorded me.

'Do you really want to wear my lingerie?' she asked.

'Oh God so much, honey, I love wearing women's underwear! It gets me so turned on! I want to be a sissy girl!' recorded me confessed. Watching it, my face turned red and I felt my cock was even harder, sliding in the panties.

More fast forwarding as she apparently dressed me in what I was wearing when I woke up. There was more kissing, more encouragement.

"Aaaand, here..."

'You want me to wear a big fat cock for you to suck?'

'Yes, very much... I love cocks... I'm such a sissy slut! I wanna be a cum dump cocksucker...'

I closed my eyes. Yeah, I'd told her everything.

"Aw, don't you want to see the rest of the movie?"

"I've seen enough."

"No. No you haven't. Look."

I opened my eyes to see her fucking me with a strapon doggy style, the dress pulled up and the panties pulled down. Her strapon cock was easily twice the size of my own cock. I was moaning and begging to be fucked harder and in less than a minute I could see my small cock spurting cum. I closed my eyes again.

"You really liked that." Pause. "And again!"

I peeked and saw that some guy had joined us, I was on my knees, wrists bound behind me, sucking and slobbering all over his big cock. He might have been one of her lovers from the PI's video recording but I couldn't tell. Just watching it my jaw ached and I suddenly felt like I could taste cum in my mouth.

She turned it off.

"I think we have some things to talk about," said Daphne calmly, sitting back down and drinking some coffee.

"Pretty wild night, huh," I said, face still red with humiliation. "Guess I really had too much to drink."

"Did you have too much to drink when you stole your sister's underwear and sucked a cucumber like it was a cock until you creamed her panties? Did you have too much to drink when you let yourself be a cock-sucker for your college roommate while wearing a dress for a year? Did you have too much to drink when you went lingerie shopping for yourself all through college? Did you have too much to drink when you would take my underwear to wear and cum in?"

I lay there defeated. She must have given me something to take down the walls I'd hidden all this stuff behind. I didn't even admit this stuff to myself though hearing her list it off made my memories of it all too real.

"What do you want?" I asked, realizing this was her game. She had all my dirty secrets and video of me doing all these things. I was effectively retired so I didn't have to worry about money but if any of this got out, my reputation in Los Angeles would be that of ridicule. My carefully cultivated friends among the elite, celeb, and powerful would vanish.

"Well, that's a good start though you will address me properly," she said with an edge to her voice.

Swallowing hard, I remembered enough from last night.

"What do you want, Mistress?" That brought a wicked smile to her face.

"So much but yet not very much at all. Get along with the new world order here and you'll be just fine. In fact, you'll be ecstatic embracing your real desires at last without having to hide them like a pussy."

I waited.

"First, you are going to nullify our pre-nuptial agreement." My eyes must have bugged out but I bit my tongue. "You aren't going to hold my financial security or quality of life over my head any more."

"If you hadn't started fucking other guys you wouldn't have had anything to worry about!" I barked without thinking.

"And if you weren't a pathetic, thimble-dicked, sissy for a lover..." she retorted before catching herself. "Sissy, this can go very well for you or very hard. If you ever speak like that to me again..."

I was angry, desperate, and trapped both figuratively and literally. "Or what!"

Biggest mistake. She got something from a duffel bag by the closet, came over to the bed, yanked down the panties I was wearing, and pinched the base of my cock.

"Hey, stop it, Jesus..." you get the idea. Within moments, my hard-on was gone. With deft fingers she assembled some multi-piece thing around my cock and balls. When I heard a click, I knew I was really fucked. She'd put me in chastity and locked it. I might have a little cock but I still love to get hard and cum. Now I was a tiny bump barely marring the smooth front of the panties she pulled back into place.

"That's just step one. Want to see step two already?"

I had to work hard to calm myself. I had to stop reacting and just play this out. She would eventually have to release me and I would put a stop to all of this.

"No, Mistress."

She gave my balls a tight squeeze making me yelp but then went back to her coffee.

"First, nullify the pre-nuptial agreement. Second, put all of your accounts solely in my name. You'll do both of these today. I've already set up a meeting with your lawyer and your accountant for us this afternoon. Once again, if you behave yourself, this can be very nice for you."

"Mistress?"

"Yes, Sissy?"

"Mistress, will you remove the chastity please?"

"No. You'll be in chastity for a minimum of two weeks and I will release you if you've shown two weeks of perfect obedience, performance, and loving deference to me. Any transgressions and the clock starts over, doubled."

My face must have looked as bad as I felt.

"Do you want me to make it a month, Sissy?" she snapped.

"No, Mistress, thank you, Mistress."

"Good. Now we have a few hours before we need to get cleaned up for our appointments. We can discuss your chores tomorrow. You've had enough of a shock for today. In fact, just to show you that I'm a loving wife and caring mistress, we can have sex!"

I knew not to open my mouth. She let her wrap fall to the floor and I had to admire how well she filled out the satin teddy. Her d-cup breasts were what first caught my attention with her before I asked her out. She did keep in excellent shape and had never failed to get me hard, wanting her.

"oooohhhghg," I groaned as my cock tried to get stiff but was contained in the tiny plastic cage. Daphne unsnapped the crotch of the teddy, straddled me on the bed and began to grind her pussy against my caged cock.

"Come on, honey, give your wife the big hard one. You fuck me now and I'll forget all this..."

I was mortified, so deeply humiliated and I bit back all the things I wanted to say. The shame of it just got me more horny which made it all worse.

"Come on," she begged, stimulating herself on the cage. "Please, gimme that cock, baby!"

She kept up this farce for another minute, frustrating me to the point of blurting something else that would make my life worse. Luckily she moved up to straddle my head and planted her wet pussy on my face. I didn't need orders from my mistress to lick, lap, and suck her folds and clit passionately.

She was very wet. My brain tucked away that bit of information as she ground her pussy on my face. She was getting off on all this.

I heard her distinctive squeal and felt her body spasming and pulsing as she had a really good orgasm on my face. It had been a long time since she'd cum like that with me, if at all. In some tiny way amid the total disaster my life was becoming, I was happy I made her cum.

"Good Sissy!" she praised and kissed me on the cheek. I'd tried to meet her lips to lips but she just shook her head.

"I... know... what... you... want..." she said in a sing-song voice, clearly flush with satisfaction and pleasure and feeling magnanimous. She went to the doorway and called downstairs.

"You can come up now."

"Daph... Mistress... please... don't let other people know about..." I began, pulling against my restraints feebly.

"Don't you worry, Sissy. They already know everything."

Not the answer I was hoping for. I laid there, crushed and resigned to my situation... for the moment.

I did not expect Eloise to walk through the door with a mimosa in her hand. When she walked over to Daphne and gave her a big kiss on the lips, some pieces started to fall into place.

Daphne embraced her with one arm and looked over at me. "Yeah, I made her a better offer..." she teased. The way Eloise was acting, she was clearly a lesbian, something I'd never even bothered to pick up on.

Next came the man from the late night video.

"Sissy, you've met before but you might not remember properly. This is Tony. Tony and I have been fucking for what... six months? Just can't get enough of his outrageous cock, can I? Well, after last night, I know you can't wait to have that cock too. And since I'm so generous as a Mistress, I'll let him have you for awhile."

With that, Daphne kissed Eloise and the two of them went into the master bedroom's bathroom, closing the door. There was giggling and the sound of our shower but my attention was drawn elsewhere. Tony was undressing.

"Tony!" I whispered loudly. "Tony, please. You don't have to do this. Find the key to let me loose and I'll make you a rich man. Please help me!"

Tony just chuckled and flexed his robust muscles as he pulled off his t-shirt. "I'm already set up for life thanks to your hottie of a wife, but thanks for offering." He unbuckled his pants and took them off leaving him in boxers that had an obscenely large cock bulge in them.

"Since you're the best cocksucker I've ever had, why would I give that up? Now open wide..."

His cock looked enormous as it neared my face then ran across my lips with precum until I opened my mouth. Oh fuck it was huge. My jaw ached holding my mouth open that wide and he easily filled my mouth with half his length.

"Hmm, I wonder when you're going to start practicing deep throating me like you promised last night," he mused as he made shallow thrusts that stuffed my mouth with cock. He slipped out and I caught myself craning my neck to keep his cock in my mouth. Moving 'above me' on the bed, he started again but now had a much better position to tease my throat.

He was patient and gentle, probing, teasing, pushing a little more each time. When something shifted and my gag reflex went to sleep I felt his fat cock head push into my throat, making my neck bulge.

"Oh fuuuuuck," he moaned and my eyes were wide as I felt his balls against my face. I'd taken him all! He enjoyed the feeling for a few seconds and then withdrew. I coughed a little and rushed to breathe a few times, strands of saliva stringing from my mouth to his monster. Then he repeated the move, slow and steady. My cock was desperate to get hard but that cursed cage kept it in painful obedience.

Before long, Tony was throat fucking me and I felt amazing! The dress, the lingerie, the bondage, and now his cock... it all made me feel like a total sissy slut and I loved it! Why had it taken so long for me to indulge this?

"Fuck! Fuck! Oh god!" blurted Tony and he held his cock all the way in. I felt it swell and throb, making my eyes water as his cum shot down into my belly. It took awhile so when he pulled out I was gasping and choking and crying. He checked on me to make sure I was okay and I recovered quickly. But I had an overwhelming need to cum.

"Please, please let me out of the chastity just for a minute! I wanna cum so bad!" I begged.

"Sorry, sissy, she's got the key around her neck and I wouldn't mess this up for anything. You are an amazing cock-sucker but fucking your wife until she spasms on my cock will always come first for me."

He went over to the TV control and looked for something else on the cloud. "I mean, once you see it, you'll agree that she and I are great together."

The TV cleared to a picture of a ritzy hotel room. Daphne was down to her panties lounging on the bed looking like a sex goddess. I moaned. I might be a total sissy but I still wanted to fuck her. And in my own stunted way, I loved her.

Then Tony came into view on the screen, naked, his big cock hard and swaying in front of him. Daphne's face lit up which was sort of a knife in my heart but it also made my cock ache in my cage.

"It's recording?" she asked, looking up at the camera.

"Yeah, babe." He walked to the side of the bed and she started stroking his cock.

"Bill, this is a cock. What you have isn't worth anything. It isn't a cock. Maybe it's your clit!" she joked, the idea just coming to her. Apparently this had been recorded months ago. "And since you aren't a real man, even with your bazillions of dollars, I had to find a real man to satisfy me. I'd tell you to learn but since you don't have a man's cock, it wouldn't do you any good..."

With that she started sucking his cock, with more passion and skill than she'd ever shown me. Clearly his size thrilled her and I couldn't blame her. His cock felt so good filling my mouth and it made me feel good to make him cum. She stopped before he came and put her ass in the air. He pulled down her panties and slid his cock into her pussy. With each thrust, she gasped as his cock apparently bumped her cervix, something I could only dream of doing.

I lay there, watching Tony give my wife an expert fucking as he lounged in a bedroom chair drinking the second cup of coffee. Moans were coming out of the bathroom but the shower was still on. I heard Daphne talking on the recording.

"Fuck you, Bill," she grunted. "Fuck you and your mind games. Fuck you for only wanting a trophy wife and not love. Fuck you for making sure I knew you could take all the money away. Here's what you deserve, you fucker. Watch him... oh fuck... watch another man... oonnnnnh... man make me cum like... oh fuck oh fuck... like you NEVER will!"

With that she began to wail, her body shaking as a powerful orgasm overcame her, Tony blasting a huge load of cum directly into her pussy. I realized that he'd not been wearing a condom. Daphne and I hadn't really planned to have kids but we didn't fuck with protection, at least back when she still let me try to fuck her. I'd had tests done and I had a really low sperm count (no surprise). I realized that Tony might get her pregnant and I'd be raising their child in my house with my money. It was also clear that Eloise was in on this and along for the ride. In the matter of a day, my life had transformed tremendously. My head was swimming and part of it was from the parade of fuck videos Tony and Daphne had shot which appeared to be playing one after another on the TV.

Eventually, Daphne and Eloise emerged from the bathroom in panties, clearly flush from sex. They flopped on the bed on either side of me while I was still mostly immobilized by the bondage. They began teasing me in the dress and lingerie until I had to moan from the ache of being unable to get hard.

"Now, once all the papers are signed today, we're starting fresh. Tony and Ellie are moving in. You won't be sharing this big bed with us. We're making up one of the guest rooms as the Sissy Room. While I'm going to be spending my time with my stud, Ellie will be teaching you and transforming you. You have a lot of shopping to do and unless you want to be recognized in all the lingerie, women's clothing, and shoe stores you'll be going to, I suggest you cooperate with her. She spent ten years working as a makeup artist so you're going to look like a pretty girl in no time!"

"Just to show you how excited I am for our new future, dear husband, I'm going to give you a gift." She reached down, unlocked and removed the chastity. My cock swelled to its full 5 inches.

"Wow, you were right," commented Eloise from my other side, poking my cock with a finger. I couldn't argue that it wasn't tiny.

I pulled on the bondage. "Do I get out of this so I can have some fun too, Mistress?" I asked as meekly as I could. Daphne rolled her eyes.

Tony got on the bed between my legs and I saw his cock was fully hard again. I watched him slather it with lube. Daphne loosened the ankle restraints some but kept them on me. She and Eloise lifted my legs and pulled my panties down to my thighs. They placed my ankles on Tony's powerful shoulders and I felt the head of his cock at my asshole.

"Now, sissy, this is the only way you'll be allowed to cum from now on. So enjoy it. If you haven't cum before Tony, it's back in the cage!"

I moaned and whined as I felt his cock penetrate me, filling me, fucking me. I felt my lingerie and dress, my high heels, the bondage. Daphne and Eloise were egging me on, teasing my body with theirs, pushing their breasts in my face, saying teasing things about their cock-sucking sissy. Tony was doing his part giving me a royal fucking until my body was shaking from his thighs smacking my ass. I gasped just like Daphne when I felt how deep his monster was getting inside me.

To my surprise, my cock was getting harder and harder, even red. With Tony's thrusting it swung up and down. I was desperate to touch it, to stroke it, but I couldn't get my hands free.

When Tony started to get faster, building to his own orgasm, I felt my body tense up. It was much more than the moments before my typical orgasm. my whole body tensed and flooded with pleasure as I felt his huge cock sliding in and out of me. I was wailing with joyous pleasure when I felt my cock spasm. The first jet of cum splattered me in the face, cum all over my mouth. The next several painted a path down my sissy dress. Tony stopped, deep inside me and pumped his own cum in me moments later.

My attorney and accountants were shocked at what I was telling them later today. But I love my wife and she loves me. Why would I ever worry about her taking care of all the money?
 
SweetAnnie40 said:
Have you introduced a sexual partner to a new kink they never tried before?


I just introduced a virtual sex partner to pegging (and feminization!) The pegging was quite well received and I think the feminization is as well.
Click to expand...

Just shared the idea of a cock cage with an e-friend... she had never seen one!
 
Okay, this is for all the girls and my gurls.

Do you have brand loyalty in your undies? Is there a manufacturer that just always makes sexier things or fits you just right? Are you a Victoria's Secret girl or Soma? Or Lane Bryant Cacique?

Can't make a poll in the middle of a thread so I'll just leave it open for answers. If you have a favorite brand, do share. Once ten people have shared, I'll let you know my answer. ;)
 
As for me.......

SweetAnnie40 said:
Okay, this is for all the girls and my gurls.

Do you have brand loyalty in your undies? Is there a manufacturer that just always makes sexier things or fits you just right? Are you a Victoria's Secret girl or Soma? Or Lane Bryant Cacique?

Can't make a poll in the middle of a thread so I'll just leave it open for answers. If you have a favorite brand, do share. Once ten people have shared, I'll let you know my answer. ;)
Click to expand...

I kinda like shopping on Hanes for undies and beginner bras.......



https://i.imgur.com/lzTYfzM.jpg


Sometimes I get lacy panties for my soft gay clit..........
 
SweetAnnie40 said:
Okay, this is for all the girls and my gurls.

Do you have brand loyalty in your undies? Is there a manufacturer that just always makes sexier things or fits you just right? Are you a Victoria's Secret girl or Soma? Or Lane Bryant Cacique?

Can't make a poll in the middle of a thread so I'll just leave it open for answers. If you have a favorite brand, do share. Once ten people have shared, I'll let you know my answer. ;)
Click to expand...

No brand loyalty yet, due to home situation it's either a brand that comes through the post or I buy in a town well away from home on my travels!!

I have an increasing style preference though... from lacy or net-style that might showcase what's on offer to anyone wishing to sample... it's now fuller satin silk versions to caress my smooth flesh all day. The sensation is of greater importance than the look, though a satin covered bulge still seems to be popular!
 
I guess no reason to hold back my answer. Not sure how long it would take to get to 10 answers anyway LOL.

For every day undies, I love Vanity Fair. Their materials and fit give me sexy nylon options for plain panties. But I've been wearing Katie and Laura Panties more every day and for special sexy nights (https://www.fancysatinpanty.com/string-bikini-panties). String bikinis are my favorite and what I buy for my sissy hubby.
 
SweetAnnie40 said:
Okay, this is for all the girls and my gurls.

Do you have brand loyalty in your undies? Is there a manufacturer that just always makes sexier things or fits you just right? Are you a Victoria's Secret girl or Soma? Or Lane Bryant Cacique?

Can't make a poll in the middle of a thread so I'll just leave it open for answers. If you have a favorite brand, do share. Once ten people have shared, I'll let you know my answer. ;)
Click to expand...

For me, depends on how ‘ where I’m going to be wearing them

Started out with very stringy, lacy things. Very sexy for in bed, but sure ain’t comfy all day

Now try to find things that blend comfort, sensation and overall feel

Love the feel of pulling jeans on when wearing a thong

Love satin plus nylon

But specific brands - boux avenue, fig leaves and sparkling strawberry
 
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