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Truth or Dare Crossdressing Story
🕑 Added 2022-08-09 14:00:01 +0000 UTCRinggggggg... Ringgggggg...
"Sean, can you get that?"
"Hello? Hey Gina... what's wrong? Ok, hold on, I'll get her..."
"Katie, your sister is on the phone. She seems really upset and said she needs to talk with you."
When I heard my wife Katie pick up the phone in our bedroom, I pretended to hang up, but instead, I put my phone on mute so that I could eavesdrop.
"Gina, what's wrong?" Katie started, "is everything Ok?"
"Katie, I just found out that Danny has been cheating on me. We talked about it and he said he thought it would be best if we just break up. Can I come over? I don't want to be alone right now."
"Ummm, sure, well, hang on, actually, can I call you back in a few minutes?"
I hung up the phone and waited for Katie to come into the living room. The reason Katie had to call her back was because we were involved in a bit of playtime, something secretive that we never shared with anyone before.
My wife is an absolute hottie; she is a sexy dark-skinned filipina, 30 years old, 5'3", 110#s, 34b, has an amazingly round ass, and is an insatiable nymphomaniac. Her overly-sexual nature requires her to have a boyfriend to supplement her hunger for passion.
The reason she hesitated in telling Gina to come over was because her boyfriend, Chris, had come over and was hanging out in the living room. She didn't want him to leave, but also knew her sister needed her right now. So, she asked Chris if he would be Ok with Gina coming over, but if he could keep his hands off of her until she left. Of course, Chris said yes, but his tone was more of a maybe.
Gina is a younger and more petite version of Katie, 24 years old, 5'0", 100#s, but with slightly bigger tits. I've had the hots for Gina since the very first day I met her. Since my wife is such a nympho, she loves dirty talk and fantasies, and we often talked about me playing with Gina while Katie watched.
After Katie made Chris promise to keep his hands off of her in front of Gina, she called Gina back and invited her over.
Chris is the typical Californian surfer guy – 32 years old, 5'10", blonde haired, blue eyed, handsome, and muscular. As if this wasn't enough to excite any woman, Chris also has an 8" clean-shaven cock with very large balls.
I must be honest, I have always been jealous of Chris. I mean, my wife and I love each other, but because he is more her 'fantasy guy', as well as better hung than me, she has longer, more powerful, and more frequent orgasms when she is with him. He is also long-lasting and very Dominant in and out of the bedroom.
I am attractive, but only 5'8", not muscular, and have only a 6" dick. I am the opposite of Chris in looks; I have brown hair, brown eyes, and more of a feminine body. Additionally, I am what my wife calls a 'minute-man' in the bedroom; I am also submissive.
Using his sex appeal to his advantage, Chris told Katie to go get a pen and paper. After writing a few things, Chris handed me a list and told me to go to the store and get a few items before Gina arrived. I knew that whenever Chris and my wife were alone, something sexual was happening. The whole way to the store, I had an emotional mixture of jealousy, excitement, and pure horniness.
When I got to the grocery store, I looked at the list: Two bottles of tequila and a dozen limes. It was a very simple request, but two bottles? I knew Chris was up to something.
Arriving home, I saw Gina's car in the driveway. Instantly, my heart started racing. I knew that Chris was planning something, but I didn't know exactly what. I walked in with the liquor and saw Gina on the couch next to Katie. She was crying and hugging her sister through some muffled, sobbing sentiments about Danny. Chris was on the recliner and motioned for me to cut up some limes.
"Katie, would you and your sister like a shot? Sean bought some tequila for us," Chris offered in a compassionate voice.
Right away, I knew Chris was being a gentleman only to gain Gina's respect and comfort.
"Yes, please," Katie, said. Then turning back to Gina she continued, "In a few drinks you'll realize what a loser Danny is, so don't even worry about him."
I fetched four shot glasses and cut up some lime wedges. Trying to be fancy, I slit the limes in the middle and placed them on the rim of the tequila filled shot glasses. I handed one to everyone and then went to get the salt.
As my back was turned, I heard Gina's sobs come to an end as she commented, "I've had a tequila sunrise, but I've never done a shot of tequila before..."
Before she could finish, Chris and his Dominant personality interrupted, "Don't worry, I'll show you the right way, Gina."
Damn, I thought to myself, 'he's already starting with his lines.' I knew what was coming...
"Here, Sean, give me the salt," Chris ordered. He licked the top of his thumb, sprinkled some salt on it, licked it, drank it, and sucked the lime. "Gina, give me your hand," Chris asked very sweetly. Then, he licked her thumb, sprinkled some salt on it, told her to lick the salt and drink it. After she had finished it, he placed the lime wedge in her mouth for her and told her to suck. Everyone but innocent little Gina knew what was going on.
"Wow, that was strong," Gina choked, "but i liked it!"
Katie did her shot and before I could even drink mine, Chris had ordered me to fix another round. An hour and several shots later, all Gina's tears turned to laughter. We were all having fun, mostly at my expense; Chris kept using me as the butt of his jokes. I acted embarrassed, but deep down I loved it. Another hour passed and we all had a really good buzz going when Chris suggested we play a game.
"Did you guys ever play truth or dare in high school? I've always wanted to do that again. Now that we are all older, it would be curious to see what kind of questions and dares we'd come up with," Chris' idea intrigued us all, but no one seemed more excited about it than Gina.
"Sounds fun," Gina giggled, "I used to play that at slumber parties, but I always thought it was kinda boring because everyone was always too chicken to make it really interesting. So, how do we get started?"
"Well," Chris took control, "Before we start, does anyone object if we make it REALLY interesting?" No objections sounded in the room, so he continued, "Ok, let's see... hmm... Katie, truth or dare?"
"Umm, I'll start with a dare."
"Ok," Chris said with a grin, "Go get dressed in some very sexy lingerie and come back when you are done."
"Yes, Si..." My wife almost said 'Yes, Sir', which is how she would answer him if we were alone. The alcohol and the mood almost gave it away, but I think Gina was feeling too buzzed to really pick up on it.
Without finishing her acknowledgement of Chris' request, Katie walked out of the living room and into the bedroom. The door shut for several minutes. During that time, Chris asked Gina all sorts of questions about herself. I was getting very jealous because I felt like the third wheel in my own home.
Finally, Katie came back into the room; no one said a word, but everyone's eyes, including Gina's, were on her. She put on a black and red corset, black stockings, black garter belt, her leather collar, and a matching black and red thong. Damn, she looked sooooo sexy; this was the outfit that Chris bought her last month for their one-year anniversary as lovers. Gina got a little quieter and acted shyer now, but I kept noticing her glancing at the sexy outfit her sister just put on.
Now it was Katie's turn to choose someone. "Chris," Katie asked in a sultry voice, "truth or dare?"
"I'll choose truth."
"Very well," Katie responded, "Do you think my sister is hot?"
Gina started blushing right away. I could also see by her little glances at Chris, while awaiting his response, she found him attractive and was hoping he would say yes.
"No..." Chris hesitated, "She is SUPER FUCKING HOT!"
Now Gina really started blushing. She could tell he was being sincere, but still, she figured it was nothing more than innocent fun; nonetheless, I could tell she was falling into his charismatic control without even knowing it.
Back to Chris; he focused on Gina. After a quick 'truth' response from her, he asked, "Gina, what's something that makes your pussy dripping wet?"
I was expecting Gina to be all quiet and maybe even avoid answering, but no...
"You wanna know what gets me wet? Big, shaven cocks!"
Oh my, I couldn't believe she said that! Was it the alcohol? Was it Chris' hypnotism? In the five years I knew Gina, I never heard her talk like that.
Gina then turned to me, and without her having to ask, I said, "Truth."
"Sean, tell us one of your kinky fantasies."
Even hearing Gina talk like that to me made my dick start growing. Adjusting myself so as not to reveal my hard-on, I started to confess, "Well, I've always wanted to be submissive in front of other people... like, be a servant boy... serve drinks, massage the ladies feet, and do whatever else they ask..."
Chris rudely interrupted, "Kinda like you served us before, sissyboy?"
I just laughed it off and said, "Sure, like before." Inside though, I was once again boiling mad at Chris and boiling with sexual excitement at the same time.
Now, it was my turn. I turned to Gina and waited for her response. She chose 'dare'. "Show us your tits, Gina, and leave your shirt off."
Gina took off her shirt, then her bra, and bared her beautifully full and perky tits. She had very dark brown nipples that were as huge as her sisters. I was so turned on by now, I would have done anything that anyone dared me to do. I could tell that the game was going to progress to a level that I only fantasized about.
No longer were we even asking 'truth or dare'. Now whoever's turn it was simply gave the request and it was to be fulfilled.
"Chris," Gina said in a sexy voice, "Show us your cock!"
Chris stood up, unzipped his pants, took them off, and revealed is huge cock. His large mushroom head poked right up as soon as it was released; his full balls hung down low. Gina perked up when she saw not only its size, but that is was totally shaven as well.
"Gina," Chris inquired even though he knew the answer, "is this the kind of cock that makes you wet?"
"Yes!"
"Then suck it!" Chris grabbed Gina's hair and pulled her mouth right onto his mushroom head. Gina sucked and sucked, all the while Chris was popping his cockhead in and out so that it made sloppy noises. After several minutes, he released her hair and Gina's spit drooled all down her tits.
Gina then looked at me and asked her sister, "Have you ever fucked Chris?"
There was silence in the room. "Yes, I have," was the only words said. After another moment of silence and several awkward but curious stares from Gina, Katie looked at me and said, "Confess to Gina what you have been doing in her hamper for the last few years and what you like to wear around the house."
For the first time, I was speechless. I couldn't believe what my wife just asked of me. On one hand, I felt betrayed that she would make me reveal such a humiliating thing; on the other hand, I had never been so turned on in my life. A fantasy was coming true and it all happened so fast and unpredictably. The rush of emotions and adrenaline were so overwhelming I couldn't even speak.
Finally, Katie told me, "Since you are too much of a pussy to say it, go RIGHT NOW and get your 'outfit' and Gina's panties that you have been stealing from her!"
Gina's face looked shocked! Pure shock! Oh my, was this going to turn bad? Was Gina going to freak out on me? I ran to the bedroom and got my things.
Returning, Katie instructed me to 'show and tell'.
"Gina, this is my French maid's outfit that I have to wear around the house, especially when I am cleaning. Your sister makes me do all the chores around here. I am her slaveboy; I am also a sissy. I have been, umm," I stumbled, choked up, and stuttered, "umm, Gina, I have been, umm, stealing your dirty panties since I met you. I sniff them, lick them, and wear them when I am cleaning the house." My face was flushed with embarrassment.
"YOU BASTARD!" Gina yelled, "For five years I have been wondering why every few months I am missing a new pair of panties! Show me which ones you have, and you better give me money for all the panties I've had to replace!"
"Yes, Gina, I'm sorry. Here, look," I proceeded to show her each and every pair I had stolen over the last five years, about twenty pairs in all. I was ready for Gina to storm out and never to talk to me again when all of a sudden...
"Sean," Gina said sweetly, "Do you really like my panties that much? Do you feel sexy in them?"
"Yes, Gina, I do," I started, "And I truly am sorry for..."
Gina cut me off to say, "Well, then, it's Ok. I've always wished Danny were more open-minded and sexually adventurous. I kinda like knowing that I turn you on that much, and that you would want to do that."
Feeling both relief and the rush of her acceptance, I felt renewed and once again ready for anything.
"So, it's my turn again, right? Ok, Chris," I said meekly, "would you tell us one of your fantasies."
"One of my fantasies? Well, I have one that's only about an hour old," Chris paused, "I want to fuck two sisters!" Without any more pauses, he continued, "Now, Katie, I want to see you kiss your little sister! Make sure it is deep, passionate, and sexy!"
Without hesitation, Katie walked right up to Gina, ran her fingers through her hair, and started kissing her more intimately and passionately than I had ever seen her kiss before. My wife and her sister kissed for many minutes and even started fondling each other's breasts. It was the most beautiful thing I had ever seen. For once, both Chris and I were completely in tune with each other; we were both mesmerized by what we were watching.
After the kiss ended, Katie and Gina had a hard time looking at each other, but the game went on. Katie said to Gina, "Since we have pretty much broken all barriers tonight, why don't you strip fully naked, Gina, and show us your whole body, including your pussy and asshole."
Gina stripped and danced around for a bit. Her tight young body was starting to glisten with sweat from all the excitement. After a few rounds of stripper-like moves, she turned around, bent over, and spread her cheeks. Chris seized the opportunity; he spanked Gina a few times and then put his finger in my wife's mouth. He gently started fingering Gina. Soon Gina was letting out soft moaning sounds. Chris withdrew his finger, told Gina to turn around and sit down, and put his finger back in Katie's mouth to suck clean.
Gina then told me to strip and show my body. When she saw my dick, she chuckled and said, "Well, after seeing Chris' cock, I don't need to look at that dicklet. Put my panties on as well as your maid's outfit."
Without argument, I did as I was told. As I went to give my next idea, Chris interrupted me, "Gina, when Sean is dressed like this, your sister calls him Stacey. So, I think we should show Stacey the difference between a REAL man and a sissy. Stacey, go kneel in the corner facing the wall, NOW!"
Chris' command was barked out so firmly, I crawled right into the corner and faced the wall. For the next hour I heard all sorts of moaning and orgasmic cries. Finally, Chris said he was taking Katie to their bedroom and that this was my opportunity to have some alone time with Gina. Meekly, I approached her. Gina pulled my hair right into her freshly fucked pussy and made me eat her out.
When the moans from the bedroom intensified, Gina cried, "Fuck me NOW! Fuck ME!!!"
I slid my dick into her warm, wet, sloppy-loose pussy and pumped away. Unfortunately, I last only 30 seconds. I came like I have never cum before! I could feel my cum gushing out so powerfully; yet, Gina hardly gasped."
"That's IT? You're done?" Gina complained. "Now I know why my sister has Chris!!! Well, have a good night." She stood right up, walked into the bedroom, and locked the door.
I was left alone for the rest of the night; I tried to fall asleep, but I just couldn't. The sounds coming from the bedroom kept me up all night.
I knew then that I would forever be nothing more than a sissy. Gina lost all respect for me after that night, but continued coming over whenever Chris was around. She never cried over Danny again!
