Becoming a Sissy
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by email@example.com (edited)
In the past few months I’ve been curious about myself. I’m a straight guy, always have been, but that’s not to say I’ven’t had fantasies about trying something new. A girl I dated a few years back was a big dick freak. She was very dominating and loved forcing herself on me, both in private and public. She would tie me down and penetrate my ass with her vibrators, while rubbishing my inadequate dick.
I grew to really enjoy the humiliation she would put me through. I would sometimes beg for her to buy a strap-on and take things a bit further, but it never happened. I never even had a thought about substituting the vibrator with a real dick until recently. Just out of nowhere these fantasies are been popping up in my mind.
I’ven’t shared these fantasies with my wife because I never planned on acting on any of these ideas. But to satisfy my curiosity I started to watch some bisexual porn, both one on one and in threesomes. It worked for me, but increased my desire for it dramatically. I loved the humiliation that was forced onto one of the guys.
One day while my wife was at work I had gotten really horny and decided to watch some porn. I came across something different than my usual videos. This one was about a guy being forced to dress in women’s clothing and being taken by a group of men and women. Cross-dressing had never really been something that sparks my interest, until now. I watched a few more videos that had cross-dressing themes just to get a feel for what it was about.
I’m a tall and thin guy with a small dick (4” erect, 1.5” soft, & erect girth 3.5”). I’m six feet and a hundred forty pounds. I’ve the build of a tall, slender female, minus the tits. My wife, though short, is still slim in the waist so fitting into her underwear shouldn’t be an issue. I decided to give it a shot. If I didn’t like it then that was that, no harm done. I went into her drawer and pulled out a few pairs of panties. The first I tried on was a sexy pair of bright blue panties. It fit perfectly around my waist and felt great on my cock. Everything fit in these perfectly.
Looking in the mirror and seeing myself really set me off. I had to take care of this hard on. I grabbed my cock and masturbated right there on the spot. I kept my dick inside the panties the whole time. The feeling of the lace rubbing up and down my shaft was nothing like I’ve felt before. It didn’t take me long to cum and when I did I just let it soak into the lace. It was an amazing thing, seeing myself in the mirror with cum soaked panties.
I couldn’t let my wife know what I did so I put them in the wash to get cleaned. This became a normal thing for me for the next couple of weeks. I would try on a new pair, cum in them and put them into the washer. One day I got the craving of wanting to feel something in my ass. It has been a long time since anything penetrated my ass, but thinking back just brought back the memory of how great it felt.
I went through my wife’s toys and grabbed one of her vibrators. It was only five inches long and maybe an inch wide. I would sit on the floor on my hands and knees and use on hand to pleasure my ass with the toy for a few minutes. I would keep the panties on and just work around them. When I was ready to cum, I would just flip over and spray all over myself. I would even watch some porn while doing this to get better pictures in my mind.
One day after a long, stressful day at work, I was looking forward to going home and having a good session with a new red thong that my wife bought yesterday. She wouldn’t be home for about two hours after me so I knew I had time to really enjoy myself. The whole ride home, I was thinking about how it would feel. I planned on using my wife’s larger nine-inch dildo this time.
As I pulled up to my apartment, I noticed that my wife’s car was in the parking lot. She must’ve finished work early. This disappointed me a little bit, but it is what it is. When I entered the apartment, I saw my wife sitting on the couch with the laptop in her lap. I heard the moaning of sex from the speakers. She looked up at me with a little anger in expression.
She held up a pair of panties that was crusted with my cum. “I found this two weeks ago,” she started to say. “I was wondering why there’s cum on them?” I knew it wasn’t from me because when we fuck I always take them off. So I decided to set the webcam to record while I went to work. I came home to see this last week.”
She turns the laptop to face me. It was a video of me masturbating in her panties, fucking my ass with her vibrator and watching a porn of a guy dressed as a school girl being fucked by another guy. I just stood there not sure what to say. I was bad enough that she found a pair I forgot to wash, but seeing a video was just really bad.
“How long have you been doing this, Jack?”
“Almost two months,” I responded, embarrassed.
“For two months you have been cross-dressing, watching gay porn and fucking your ass with my toys?” She asks while she closes the laptop.
I don’t respond. I just stand there with my head hanging down. She stands and walks towards me, cum covered panties in hand. She holds them up and pushes them into my face. I lean back to try and get away, but she just closes the distance until they are against my nose.
“I’ve been thinking of what to do for the past week about this. I’m going to hold on to these as they are and the video is saved and backed up in different locations. If you don’t do as I say, I’ll upload the video and email it to everyone we know. Do you understand?”
She lowers the panties from my nose and looks at me with anger in her eyes. “Yes,” I say. “Just don’t show that to anyone, please! It would ruin me. What do you want?”
“First, you need to shower,” she turns and walks back over to the laptop.
I stand there confused as to what she had planned. She returns to the laptop and starts the video of me again. She watches closely. At the same time I see her typing something. I can’t make out what it is or if it’s for someone.
She looks up at me, and says, “Shower… NOW!”
I head to the bathroom and get into the shower. A minute or so later, while I’m rinsing out my hair, Mary walks into the bathroom. She opens the shower door and says, “I want you fully cleaned, shaved also.” She hands me the razor and shaving cream. “I don’t want a single strand of hair on your body except for your head.”
She closes the door and leaves the bathroom. It takes me another twenty minutes to shave my face, chest, legs, balls and ass. I step out of the shower, dry off and walk into the bedroom. I get out a pair of boxers and start to put them on. When I get one foot in, the door to the bedroom opens and Mary walks in.
“I don’t think men’s underwear is good enough for you anymore. Put these on.” She throws a pair of neon green silk and lace panties at me. “I bought this as a special gift to wear for you, but seeing as you like to wear my shit, you can try them on first.”
I’m hesitant to put them on but slowly get them up around my waist. They fit better than any I’ve worn before. The back was silk and formed to my ass perfectly ending about mid-cheek. The front was see-through lace and fit around my package nicely. The material felt great and I started to get hard instantly.
Seeing my cock grow, my wife shakes her head a bit aggravated. “I can’t believe this gets you turned on faster than seeing me naked. You’re a babydick sissy, aren’t you?”
I just stood there with a fully erect 4″ cock bulging out against the panties. I was taken aback by her words. I didn’t know how to respond.
“I asked you a question, sissy! You love dressing up like a girl, don’t you?”
I nod, and say in a low voice, “Yes.”
“Get on the bed on your stomach,” Mary demands. I do as she says. “For the past few days, I’ve gone through your internet history and watched what you watched. I’ve come to the conclusion that you really love the idea of something in your ass.”
I hear her walk over to the closet and open the door. I couldn’t see what she was doing, but I heard a bag. She walks back over to the bed and drops the bag on the floor. “So I went out and bought a nice toy for you. It’s a little wider than my small vibrator, but from the looks of the cocks in the porn, you’ll want something bigger than even this.”
Mary pulls the back of my panties aside, spreads my cheeks apart and spits directly onto my hole. “You want to dress like a bitch, you’ll be treated as such.”
She shoves the toy into my ass with a great amount of force and very little lubrication. I cried out in pain as my hole was split open. “You’ll keep this plug in your ass until I say otherwise, got it?” She says to me, as she pushes the plug in as far as it’ll go.
“Y-Yes,” I respond with pain in my voice.
The butt plug looked twice as wide of what I was used to, and maybe four inches long. I always used a ton of lube and worked my asshole open slowly with my pinky finger. She fixes the panties and steps away from me.
“Now get off the bed and kneel in front of me, sissy!”
I do as she says. Kneeling in front of her, she undoes the button of her pants and takes them off. She grabs my hair and pulls me towards her crotch. “Eat my pussy until I cum, sissy boy.”
With my back to bed, she grinds into my face with such force I’m pushed back and down onto the heels of my feet which push the plug in deeper. She holds my face against her pussy as I lick. I try and pull back to catch a breath, but she just pulls me back in before I could get a full breath. Her moans grow louder and faster. She pushes as hard as she can into my face as she shakes with the oncoming orgasm. Applying more pressure to my face, she pushes my head back against the bed. As she cums, she grabs my hair pulling me closer. Once finished, she pushes me away and pulls her pants back up.
“You can stand and finish getting dressed. We’re going out.”
Mary walks over to where our clothes were kept. She opens a drawer and grabs a pair of her jeans. Then she reaches into the closet and pulls out a black T-shirt that had ‘Horny’ in pink letters on the front. The T-shirt was a bit small, ending at my belly-button. She throws the clothes at me and leaves the bedroom. I get dressed quickly. The pants are very tight fitting and don’t cover my ass completely. The T-shirt is also tight. I look in the mirror feeling somewhat embarrassed by myself.
I exit the bedroom. I’ve never shaved my whole body before so the feeling of smooth skin against my clothes seems very stimulating. My wife is standing by the door ready to go. She looks at me and shakes her head. “Well, that won’t do.” She walks toward me, reaches behind and pulls my panties up above the jeans. She leans in close, and whispers into my ear in a very seductive tone, “You need to show off your panties, like a good sissy.”
“I don’t want anyone to see that I’m wearing this,” I respond to her.
“If you can’t be seen, I won’t be happy. If I’m not happy then bad things happen to you.” She sucks on my ear for a moment. Looking down, she sees the bulge in my pants. “That’s what I thought.”
“What do you have planned?” I ask curious about her intentions.
“If I told you that would ruin all the fun!” She grabs my ass cheeks and pulls them apart, putting tension on the toy buried in me. “Let’s get going.”
We leave the apartment and get into the car. Mary’s vehicle is an old Jeep Wrangler. With the top and doors off, everyone would be able to see panties peeking out of my pants. I moan at the feeling of the plug being pushed deeper as I sit down. My wife looks at me with an evil smirk. “Seeing as you love the feeling, I’m going to hit every speed bump and pothole along the way.”
She speeds away, heading towards downtown. I can feel the back of my pants are low, exposing the neon green panties to the public. Of course we are stopped at every red light the time we were driving. At every light, another car pulls alongside and the driver looks over. I can’t tell if they see anything because I never look back. I couldn’t bring myself to know. After driving, in what seems like circles, for a bit, she pulls into a parking lot of a bar. She parks the jeep in the back far corner.
“Can we please go somewhere… less public? I agreed to do this so no one would see what I’m wearing?” I try to plea my way out.
Mary turns the car off and looks at me. “You agreed to do this, so I wouldn’t upload you fucking your sissy ass while watching gay porn!”
She opens the door and gets out. I follow shortly after. We enter the building and Mary decides that we need a seat at the bar so I can be seen. She picks a seat that can be viewed by anyone entering the bar. As I sit I try and pull my pants up and shirt down to hide the obvious. “I don’t think so, sissy,” Mary says.
She reaches over and pulls the back of my pants down enough to show almost two inches of the bright green panties. She grabs my shoulder and pushes me down onto the wooden stool with enough force to push the plug in deeper.
I squirm slightly, trying to get used to the feeling of having something in my ass for this long. Mary smiles as she notices my discomfort. The bartender walks over, and asks, “What would like?”
As I start to answer, Mary cuts in. “I’ll have a beer, and she’ll have an Appletini.”
She smacks my ass lightly in a teasing matter. The bartender looks at me and laughs before walking away to get our drinks. “Did you have to say that?” I ask Mary.
She just giggles and looks around the bar. “Oh, sissy, a lot of people are noticing your sexy underwear!”
I lower my head, trying to hide my face. Out of the corner of my eye I can see a few people looking at me. Some are laughing and pointing it out to the people they are with. Others are just staring, waiting to see what else was going to happen.
A few minutes go by and the bartender brings us our drinks. “You’re drawing attention to yourself, sissy,” he says, setting the drinks down in front of us. He looks at Mary and says, “A friendly warning, you may want to take it easy showing him off. There are a few people here, both men and women will jump at a chance to get a piece of her.” He looks back at me. “And it’s obvious this is your first time. That makes it more appealing.”
He collected the money for our drinks and walks away.
“Did you hear that?” Mary says to me. “If you don’t behave yourself, I’ll find someone that will abuse your little sissy ass!”
The last part was said loud enough for the surrounding people to hear. I noticed a few move a little closer to us, hoping to get a chance.
“Drink your Appletini, sissy,” Mary pushes the drink closer to me. I bring the glass to my mouth and take a sip. “There’s something I didn’t tell you, sissy,” Mary reaches into her purse and pulls out a small black remote. “The object I inserted into you is also a vibrator!”
As I start to take another sip of my drink, Mary presses a button on the remote. The butt plug in my ass starts to vibrate violently. I dropped my glass from being startled by the sudden movement of the toy that is buried in me. The green fluid spills all over my shirt and jeans. I stand quickly and reach for some napkins to wipe myself off.
“Sit down, sissy,” my wife yells at me.
As I sit I notice that the back of my pants has fallen down a bit more. If it wasn’t noticeable enough before, it is now. The entire top half of my ass was hanging out showing more of the green panties. “How dare you spill a drink? That was bought for you! It’s extremely rude!” She had everyone’s attention at that point.
“I’m… I’m sorry… I was just startled by…” I try to apologise but she wants nothing of it and silences me with a wave of her hand.
She finishes the rest of her beer and stands. “Let’s go, sissy, you need to be punished!”
Grabbing my hair, she starts to pull me with her towards the exit of the building. Because I’m close to six inches taller than her, the force has me bent down, allowing anyone behind me a good view of my exposed ass. As we get close to the exit, a man steps in front of both of us.
“I enjoyed the show you put on for everyone to see,” the man spoke to Mary pretending I wasn’t even there.
He looked taller than me by at least four inches, close to two hundred and fifty pounds of, what looked like, solid muscle and a large bulge in his pants. “If you want to take things further, here’s my number. My name is Bill. Give me a call and I’ll do anything you need.” He looks at me, smiles and turns back to my wife and continues speaking. “And I do mean anything.”
I try to protest, but Mary just giggles with excitement and takes his number. “Maybe I’ll take you up on that.”
Bill steps aside and we left.
“You aren’t going to call him, are you?” I ask her with a little anger in my voice. “This was supposed to be just for tonight. There’s no need to keep this going and bring someone else in.”
Mary turns off the vibrations of the plug and puts the remote back in her purse. “I didn’t plan on doing anything else past tonight, but you seem to really enjoy being a sissy,” she says, grabbing my hard cock through my jeans.
We walk to the car that is parked in the back corner of the parking lot. She leans against the car and pulls me in for a deep kiss. I can tell by her kisses that she’s really horny. “I want you to eat me out!”
I pull away from her and go to open the door to the car. She pushes me away from the door and slams it shut. “No, right out here.”
I start to protest because of how public it is. She stops me before I can say anything. “It’s late at night on a Thursday, be thankful I’m not having you do it during the peak of business.”
She’s right, the side of the car was out of view unless someone walked right by this way which wasn’t needed because there was nothing but a wall there. “Just warn me if people are coming.”
I start to go to my knees, but she pulls me back up. Mary walks to the front of the car, lowers her pants and sits on the hood. “But the hood is visible by anyone looking this way,” I protest.
“Then you better make it quick, and hope no one looks this way! Now get to work sissy before I make things worse for you!”
She spreads her legs apart, exposing her beautiful wet lips waiting to be worshipped.
“Mary, can we please do this in the car? I-I don’t want to risk the cops being called on us.”
I try to talk her out of it, but he just shook her head and pointed to her pussy. I try to speak again, but she cuts me off.
“Damn it, sissy,” she yells at me. “I told you I would make it worse if you argued. Pull your pants down. I want your ass exposed for the world to see how much you love wearing women’s panties. You also can’t kneel and hide yourself either. You must bend at the waist and stick your ass in the air! Get over here now before I strip you completely and call Bill to come over fuck your ass! I bet his cock is much larger than that butt plug.”
I may have watched gay porn and had fantasies of being fucked by a guy, but it wasn’t something I wanted to happen. Especially not like this. I walked to the front of the car and bent at the waist. I placed my elbows on the hood of the car and started to lick Mary’s pussy. She was so wet. The light above the car was bright enough to illuminate the area and make it obvious to anyone looking this direction to see.
She lays back against the hood of the car, allowing me a better angle to get myself deeper. I rub my tongue all over my wife’s pussy, occasionally burying it as deep as I can inside her. Mary starts to breathe faster and moan louder as her orgasm starts to build. After a minute or so, my wife arches her back and uses her feet to push her hips higher into the air. With one hand she reaches down and grabs my hair.
“Lick my ass, sissy,” she says, and pulls my head down.
I’ve to turn my head slightly and lift my ass higher into the air to get a good angle. She lets go of my hair and starts to rub her clit. As my tongue explores her hole, Mary starts to rub herself faster. After another minute or so, Mary moans loudly as her orgasm takes over. She sits up slowly trying to catch her breath. She then puts both hands on my shoulders. “Nicely done, sissy. Now get off me.”
Mary pushed me away with enough force to make me stumble back, trip over my pants around my knees and fall back onto the ground. I hit the ground with enough force and at the right angle that the butt plug was forced out. It happened so quickly that the force of it leaving made me cry out in pain. As Mary was standing and pulling her pants up, she noticed that the plug had fallen out.
She grabbed me by the hair and pulled me to my feet. She pushes me down onto the hood of the car slamming my face down onto the car. It was hard enough that I was sure it was going to bruise my cheek. “I told you to keep that in your ass, sissy! Don’t fucking move!”
She lets go of me and walks away. “You must now be punished for not listening!” Mary yells walking back towards me. “You are just lucky I don’t have anything really big on me!” Mary leans in close to my ear and whispers softly. “This may hurt a little because I refuse to lube it for you! Plus, there’s small pebbles stuck to it, and I won’t remove them.”
I feel her hand pull one of my cheeks apart from the other and I knew what was coming. I felt the plug being inserted quickly into my ass. She stopped just at the widest point and kept me stretched out. She pulled it out slowly, then shoved it deep back in. The pebbles felt like sandpaper against my hole. It hurt like a bitch. Mary started to fuck my ass quickly and very hard. I was screaming in both pain and pleasure. My cock was rock hard and in need of release. Just out of instinct, I reach for my throbbing cock.
Mary shoves the plug deep into my ass and let’s go. She grabs my hand and hair, turns me around and pushes me back down onto the car. She releases my hand and slaps my face. “A sissy is NOT allowed to cum! Try that again and the pain from the debris on the plug will be nothing compared to what I’ll do to you. Now take off all your clothes except for your panties and get in the car.”
After the abuse my ass just got, I didn’t want to make things worse.
I took everything off and handed them to her. She puts them into the back seat and gets in the car.
Just as I start to walk around the vehicle I hear a sound behind me. I turn around to see Bill standing less than ten feet away. I quickly get into the Jeep before I found out how much he saw. Mary starts the car and begins to pull away.
As we pass by Bill I can hear him speak loudly to Mary. “That show was better than the one inside. I look forward to your call.” We pass by and he yells loud enough for us to just make out his final words. “I also look forward to fucking your ass, Sissy boy!”
Not a word was spoken as we drove home. Mary had turned on the inside lights for the drive so anyone that was next to us could look in and see me, and there were a few that did. She pulled into the parking lot of our apartment and parked as far as she could from our door. There was a spot right in front of the door, so why would she park so far away?
She gets out of the car, grabs my clothes from the back seat and starts to walk towards the apartment. My wife pauses and looks back at me still sitting in the car. She yells loud enough for all to hear. “Let’s go, sissy! You need to show off your sissy body to everyone!”
She had my clothes and it was cold outside so I couldn’t just stay in the car forever. I looked around and didn’t see anyone nearby. Maybe I could get to the apartment before anyone showed up. I walked as fast as I could to our door. My cock has shrivelled up due to the cold and it was barely noticeable in the panties. I finally reached the door before Mary and was thankful that no one was outside.
Mary, after taking her time, reached our door, unlocked it and started to open the door. She enters the apartment and closes the door behind her before I could get inside. “You were in such a hurry that no one was able to see you. Don’t you want to be seen, sissy?” Mary asks from inside the apartment.
I put my hands around my cock and shiver. “No, people here know me! It’s cold and humiliating to stand out here like this! Let me in!” I reach for the door to open it.
Mary quickly locks the door and smiles. “Sissy’s like to be humiliated. So you will stand out there until I come back for you. I’ve to get a shower so it may be a little while. Turn and face the parking lot, I want everyone to see you.”
She turns and walks away, leaving me standing outside in nothing but the bright panties. It was late enough that hopefully everyone was already home and in bed. I place my hands over my cock and lean against the door. As I stand there, helpless, I start to think back on the events of this evening. My face turns red as I remember all the people staring at me at the bar. My cock started to grow with the idea of how many wanted to abuse me. The thought of being used by any number of them was very exciting.
I closed my eyes and pictured what it would be like. On my hands and knees eating out one of the women while being fucked from behind by a guy. Bending over the counter of the bar as one of the large men pulled my hair while pounding my ass. Even just sitting on my knees with all the men around me, forcing their cocks deep down my throat. All of these ideas were amazing.
I was so lost in my thoughts that I didn’t realize the car that pulled into the spot directly in front of me. The headlights of the vehicle pointed directly at me gave the driver and perfect look at my cock standing straight out against the neon green panties. Panic sets in. I can’t see who is in the car. The person sits there with the lights on for what seems like forever. The door of the vehicle finally opens and the person steps out. I immediately recognise the person and my heart sinks.
My neighbour, Alex, is a very attractive tall and thin woman in her mid-thirties. We have had a few encounters in the parking lot but never talked for longer than a few minutes. We never hung out or even spoke about our personal lives.
Now my personal life was there, naked and out in the open for her to see. She slowly walks towards me, eyes locked onto the green panties that stand out in the light. Just as she walks to her door, which is about five feet from me, Mary opens the door behind me. I turn to notice that she wore nothing but a pair of my boxers.
I quickly make for the door when Mary pushes me back outside. She leans out the door and speaks to Alex. “So Alex, what do you make of my sissy? It’s her first night out!”
Alex smiled brightly at me. I look away in shame. “I’ve those exact panties in red. If you would like, I can let you borrow them, Jack. I love the sissy look Mary, I’ve some things that would hope convert him fully.”
She winks at me and enters her apartment. Mary finally lets me inside. My face was red with embarrassment. I can’t believe that just happened. How could I show my face around here now? I’m sure the word would spread fast. Mary didn’t seem to care. She just giggled as she walked towards the couch.
“Come here, sissy and kneel in your place,” my wife orders as she sits on the couch.
I walk over and kneel between her legs. Just as I get settled down Mary turns on the plug in my ass. I close my eyes and moan in pleasure as it sends pulses through me. I reach up to pull the boxers down around her to give me full access of her pussy.
My wife grabs my hands and moves them away from the boxers. “You need to work for your gift, sissy. Don’t stop until I say,” Mary demands of me.
I pull the boxers to the side as much as I could. As I started to lick her pussy she grabs me by the hair forcing me closer in. It was difficult to get a good angle with the boxers around her waist. The inside seam was pressed tightly against my jaw and it hurt. Every time I tried to adjust, Mary would just pull me in tighter.
I brought one hand up and slipped two fingers into her. I begin to massage the inside of her pussy with my fingers while using my tongue to play with her clit. In one swift movement, Mary pushes me away, stands and takes off the boxers.
“Turn around, sit on your ass with your back to the couch,” Mary says as she grabs the remote to the toy in my ass. She turns it on to full blast. I lean my head back against the couch and close my eyes as I let the pleasure of the vibrations take over. “Get back to work, sissy,” is all I hear before Mary grabs the hair on the top of head, holds my head back against the couch and places her pussy in my mouth.
With one knee up on the couch, Mary was able to grind her clit against my nose as I licked deep inside her. Occasionally she would bend her hips out farther brings my tongue to pleasure her ass. My wife would alternate between the two allowing for her clit to rub against my face, bringing her closer to another orgasm. As her body began to shake, Mary grabbed my head with both hands, held me down with all her weight and pressed her pussy against my face.
“Don’t stop, sissy! I’m going to cum,” she yelled between moans.
The grinding of my face became faster and harder. There was no room for me to catch my breath as all her weight was against my face. My vision was starting to go black and my breathing slowed as I started to pass out. Mary screamed with an intense orgasm and flung herself off me and onto the couch. Using her feet, she pushed me away from the couch. My body twisted and landed face first onto the floor. I just lay there trying to breathe.
Finally, I was able to get my breath back. I turned my head to see my wife leaning back against the couch trying to catch her breath as well. The vibrations of the butt plug still sending shivers through my body. My balls hurt from being filled with so much cum from being hard most of the evening. I needed to cum.
I just lay there with my eyes closed still trying to recover from the near suffocation from my wife’s pussy. When I finally open my eyes, my wife was nowhere to be seen. I look around and notice that the bedroom door is open. I figured she must have gone to the bathroom. This was the perfect time me to try and cum quickly before she returned.
I quickly rolled onto my back, grabbed my cock through the panties and started to rub as fast as I could. After only thirty seconds I could feel the orgasm building. I closed my eyes and tilted my head back preparing for release. Just as I was about to shoot my load into the panties, my hand is pulled away from my cock and my wife slaps me with all her strength across the face.
“Sissy’s are not allowed to touch themselves!” She screams in my face.
My cheek burned from the hit. I could feel a trickle of blood down my cheek. Her ring must have cut me. She grabs me by the hair, lifts me to my feet and leads me into the kitchen. My eyes were watering from the slap and I couldn’t see anything. She pushes my head down onto the table and pulls my hands behind my back.
“Now you have to be punished even worse than at the bar.”
She then opens a drawer in the kitchen and pulls out the duct tape. She tapes my feet to the legs of the table keeping them spread wide apart. She then takes my hands and spreads them across the length of the table. She tapes my arms down fully making it so my ass is in the air and I’ve no leverage to get myself loose.
I had just remembered that there was a set of windows in the kitchen. These windows can be looked through from the patio of my neighbour Alex. I couldn’t turn my head to see if she was there, but I had hoped she wasn’t. She walks away from me leaving me taped to the table with my ass in the air and bright green panties to show the world.
My wife returns to the kitchen. She doesn’t speak a word to me before she pulls the butt plug out of ass. I grunt in pain. I feel a small drip of, what I assume to lube, fall into my hole, but it didn’t feel like much. Then I feel the pressure of something else against my ass. The pressure builds as my ass it spread further than it has before. I moan louder as the pain increases.
I can feel the object is already at least three inches inside me, but it keeps growing in width. Mary just continues to push the object deeper without any more lube or ease of pressure. The presence just kept going deeper and spreading me wider. I finally feel her hand against my cheeks as the final inch gets inserted into me.
“I bought this yesterday just for this occasion,” Mary whispers to me. “I wasn’t going to use it because I thought It was going to be too big for you to take. Because you were so bad today and didn’t behave yourself, I didn’t have a choice. I was clearly wrong though. I should’ve known a sissy like you could take every inch of this dildo. It starts off only a little bigger than the plug. Its ten inches long and slowly grows to three-inches in diameter.”
She works the dildo in and out of my ass and slowly picks up the pace.
It still hurt too much for me to get pleasure from, but that was the point. This was all about her. Finally, she pushes the dildo in as far as it can go and leaves it there. She cuts me loose and pulls me up from the table. I can feel the dildo starting to slide out.
She turns me around, and says, “Sit on the table. We need that to stay in you.”
I do as she says and pull myself up onto the table. The dildo slides back into me and fills my ass to its breaking point. Mary then climbs up onto the table with me and straddles my aching cock. She pulls me close to her as she rides me on the table. The back and forth movement makes the dildo stretch me out even further. My moans grow faster and I knew I wasn’t going to last long. Sensing this my wife yells into my ear, “Don’t you dare cum before me, sissy!”
Her pace increases. It gets harder to control myself. All my focus is put on trying to keep myself from cumming. After another few minutes I moan loudly and shoot a load inside her. It was the best orgasm I’ve ever had. I could feel my cum dripping out of her pussy and running down my cock and between my legs. There was so much of it. She just kept riding me trying to get herself to another orgasm. It wasn’t long until my cock went soft.
“Damn it, sissy,” Mary says as she climbs off me. “You just won’t listen.”
She pushes me back onto the table. Mary climbs up onto the table and straddles my face with her ass to my nose. My cum pouring out of her and into my mouth. The warm salty fluid filled my mouth and I gagged trying to swallow what I could. She pushes her pussy into my face making sure I don’t miss any. The position she is in giving her easy access to the large dildo in my ass.
“Now you have to clean me,” Mary says, grinding into my face again.
She grabs the dildo that’s buried in my ass and starts to move it in and out very quickly. Every time she starts pushing it back in, she tilts the dildo to the side stretching me further apart. She doesn’t let up on how hard she moves it around. I try to scream out in pain, but her pussy pressing against my mouth prevents any sounds from being heard. I was certain that my ass would never recover from being stretched so much. The smaller toy she had felt wonderful, but this was the most painful thing I’ve ever felt.
Mary just picks up the pace of fucking my ass. She goes faster and harder the closer she gets to her orgasm. She finally releases the dildo after shoving it deep into my ass. She sits up straight putting all of her weight down onto my face. She rocks back and forth grinding her pussy against the bridge of my nose. She puts one hand on my chest and the other she uses to play with herself.
“Come on, sissy, lick every last bit of your cum out of me!”
My wife uses her fingers to dig deep into her pussy and force more and more of the cum out and into my mouth and all over my face. Her pace picks up and she puts all of her weight down onto my face. My head is stuck where it’s at and I can’t move. Once again, she doesn’t care if I can breathe or not. As her pussy grinds back and forth over my nose, I push my tongue as deep into her as I can. Mary repositions herself, giving me a chance to catch a breath, then pushes her ass hole in my mouth.
“Don’t forget my ass, sissy,” Mary screams between her moans. “Get your tongue in there!”
She pushes her hole against my mouth and I work her open with my tongue. Her fingers go deeper into her pussy as she brings herself to her biggest orgasm yet. Her weight on my face is starting to hurt as I feel like the back of my skull is going to crack open against the table. Once again, I can’t get any air into my lungs and I start to black out.
“I’m going to cum, sissy! Don’t stop now!” Mary screams louder than ever.
Her moans quicken and the pressure on my face increases. My vision is gone and I can barely make out her words. My wife screams as she starts her orgasm. She lifts her pussy up off my face. I still can’t get my lungs to breathe as I slip into unconsciousness. The last thing I remember is the scream of my wife and the feeling of something spraying all over my face.
When I finally regain consciousness, I start to sit up, but fall back down from the pain in my head. I just lay there with my eyes closed, trying to gather myself. After a minute I open my eyes and look around. I’m still on the table, completely naked, my vision is blurred by the combination of my own cum that was smeared all over my face, and the juices from my wife. I can still feel the large dildo still in my ass. I use my hands to wipe my eyes clear. I lift my head and I see Mary sitting in a chair at the end of the table with a glass of water in her hand.
“You were out for five minutes, sissy,” she says after drinking her water. “I was worried because you didn’t start breathing for almost a full minute.”
She stands and walks over to me. She runs a finger along my cheek, gathering up the fluids on my face. “I’ve never squirted before, it was the most intense thing I’ve ever experienced!”
She pushes her finger into my mouth. I suck off her juices as well as my cum. She runs her hand slowly down my chest, over my cock and to my ass. She grabs the dildo and pulls it out of my ass in one swift movement. She holds it up so I can see just how large this thing really was. “I’m so happy you were able to take this whole thing in your ass, Jack,” she says sitting it on the table next to me. “Now get up and clean yourself up. I’ve to make a call before bed.”
She walks out of the kitchen and I can hear her talk into her phone as she walks into the bedroom. “Hello Bill? Are you still up for playing with my sissy?”
My eyes grow wide in shock. I thought this was it. I did everything she wanted. Was she just messing around? She wouldn’t do this. I sat up for the first time. My ass felt so empty without the dildo inside. For a moment I wished it was back inside me. As I stand I happen to turn towards the window. I suddenly remember that it was wide open and exposed to my neighbour’s patio.
Alex was there, sitting in a chair, naked. Her legs spread wide apart and her hand deep inside her pussy. I was so mesmerised by the sight of her playing with herself, it took me a moment to see what he was holding. In her free hand, a small camcorder, sat pointed into our apartment. She had recorded the whole thing that my wife did to me. This just added more humiliation to the moment. I could never risk running into her again. I had to leave before she said anything to me.
I grabbed the dildo off the table and turn to leave the kitchen. I can hear Alex moan as she cums from her patio. My face is bright red from embarrassment.
I go into the bathroom and take a shower to get cleaned up. When I finish my shower, I walk into my bedroom and see my wife already sleeping. I slide into the bed next to her and fall asleep instantly.
Things proceeded as normal the next morning. She never mentioned what happened last night. However, over the next month changes begin to show. All my underpants got replaced with panties and bras. Mary started bringing home sissy clothes for me to wear around the house and on special outings. I grew my hair long and learned how to put on make-up. Alex out neighbour has been a great help. The butt plug has to stay in at all times. She brought me a cock cage and locked me in chastity so I couldn’t jerk-off. Our sex life changed for me performing oral sex on her regularly, and her fucking me with a large strap-on dildo up the ass.
A month after we began this new relationship, Bill came over for dinner and let’s just say I experienced my first real cock and loved it. Yes, I’m a babydick sissy faggot, and I love it. I’m just grateful my wife has embraced this lifestyle as much as I’ve. I love her so much for that. Mary’s now talking about me getting breast implants, she’s so hardcore!
Loved your story ,when my wife caught me in her panties and garterbelt on my knees sucking our gay neighbors cock ,she did just asbout the same thing and I am now a panty wearing sissy cocksucker and my wife a cuckoldress who loves making me sit and masterbate in her panties as she fucks men with big cocks she picks up at the bar ,I am then made to suck her new big cocked mans cock clean after he fucks her and sometines she has him fuck my sissy ass ,so you and I are about the samne except my cock is 3 nches hard its nice to know there are other sissies controled by there wives
Very very nice love the whole sisi life style very hot
Are you a sissy to your girl or wife too?
oh very much so. i watch …in my panties and bra while my wife is sexual taken care of by her BF’s they tease me alot about being small and limp… i love it
I too am a cuck for my girl friend after being caught wearing her square dance skirt and petticoat. Now I sit in girls clothes at the foot of her bed and watch her getting fucked by other men.
God my pathetic clitty. is so hard after reading the story .i luv the idea of being humiliated. publicly and drinking pee .my goddess now makes me peemy panties. 3times a day .in the supermarket ,in the bank and. grocery store .I’m then allowed to keep. wearing them.mmmmmmmmm yummmmmnnmmy.I’m such a dirty,filthy,worthless,pathetic. pussy faggot whore.
Only thing is I enjoy being humiliated. The more my girl gets fucked by other guys the more turned on I get. She knows it too so she let’s me play with my tinny whinny 3″ dick all dressed in my pretties while she gets it on with a macho guy. I have my fun while she has hers.
Hi sissies I love these stories my little clitty throbs and my titty nipples go really hard and stand up l like two little cocks I love my sissy slutty bum hole and have stretch it and over the years with everything you could think of im only a little girly sissy all the time now shaved all that hairoff yuckies and now I’m all smooth and feminine ready for big cocks I wear lots of pink lipstick and tuck clitty away in between my legs marking all sissies feel like where ladies all girly and feminine.
Any way I was all dressed up in pink lacing petticoat bra panties etc feeling so lady like I was taken over too a table were some trannies were and all nigth I had been making eyes bending over teasing them my friend told me to say I was sorry I did and then I burst into sissy tears I went down on my hands and knees lifted up the first tranny skirt and kissed the lump inside those silky panties and made this pretty cock hard and cum in my mouth l love it and before I knew it had tranny cock fucking my sissy bottom I feel warm sexy and absolutely loving cocks . Wembii xx