Caught in Her Panties Ch. 01

In the past few months I have been curious about myself. I am a straight guy, always have been, but that's not to say I haven't had fantasies about trying something new. A girl I dated when I was 19 years old, I am now 28 years old, was a big freak. She was very dominate and loved forcing herself on me, both in private and public. She would tie me down and penetrate my ass with her vibrators. I grew to really enjoy the humiliation she would put me through. I would sometimes beg for her to buy a strapon and take things a bit farther, 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 haven'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 group of men and women. Crossdressing had never really been something that sparks my interest, until now. I watched a few more videos that had crossdressing themes just to get a feel for what it was about.

I am a tall and thin guy. Six foot and a hundred forty pounds. I have 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 rubbed one off 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 have 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 by hole, 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 three 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 seven 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 have been done 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 was cum in them. I knew it wasn't from from we would fuck because 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 masterbating 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 respond embarrassed,

"For two months you have been crossdressing, 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 have been thinking of what to do for the past week about this. I am going to hold on to these as they are and the video is saved and backed up in different locations. If you do not do as I say, I will 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 its to 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 am 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 mens 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 these as a special gift to wear for you, but seeing as you like to wear my shit, you can try them on first."

I am hesitant to put them on but slowly get them up around my waist. They fit better than any I 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 are a little sissy aren't you?"

I just stood there with a fully erect cock bulging out against the panties. I was taken back 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 yes in a low voice.

"Get on the bed on your stomach .," Mary demands. I do as she says. "For the past few days, I have gone through your internet history and watched what you watched. I have 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. Its a little wider than my inch wide 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 will 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 will 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 will go.

"Y...Yes," I respond with pain in my voice. This was twice as wide of what I was used to and maybe just under four inches long. I always used a ton of lube and worked my hole 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 down 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 am 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 are going out." Mary walks over to where my clothes were kept. She opens a drawer and grabs a pair of tight skinny jeans. Then she reaches into the closet and pulls out on of my old t-shirts. The shirt was a bit small, ending at my waist. If I moved my arms in any direction, the shirt lifted up exposing my lower back and stomach, which is why I haven't worn it in a long time. She throws the clothes at me and leaves the bedroom.

I get dressed quickly and exit the bedroom. I have never shaved my whole body before so the feeling of smooth skin against m clothes was 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 towards me and slowly takes off my belt. She leans in close and whisper into my ear is a very seductive tone, "You can't show off your panties if the pants never slip down."

"I don't want anyone to see that I am wearing theses," I respond t her.

"If they can't be seen, I won't be happy. If I am 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. "Thats 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. "Lets 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 peaking out from 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 am 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 along side 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 am 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 deep.

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 speaks to me, "What would like?"

I as start to answer, Mary cuts in, "I'll have a beer and my sissy husband here will take 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 are 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, that Will jump at a chance to get a piece." He looks back at me. "And its obvious this is your first time. That makes it more appealing." He collects 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 walk a little closer 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. "Theres 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 loudly at me. As I sit i notice that the back of my pants have 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! Its extremely rude!" She had everyone's attention at that point.

"I'm...I'm sorry, I was just startled..." I try to apologize but she wants nothing of it. She finishes the rest of her beer and stands. "Lets 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 am 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 was 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 is my number. My name is Bill. Give me a call and I will 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 will take you up on that." Bill steps aside and we leave.

"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 is 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 exclaim 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 was really horny. "I want you to eat me out!"

I pull away from her and go to open the door for 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 was. She stops me before I can say anything. "It's late at night on a Thursday, be thankful I am not having you do it during the peak of business."

She was 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.

"Damnit 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 have you strip completely and I call Bill to come fuck your ass! I bet his cock is much larger than the 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 for 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 breath 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 screams and pulls my head down. I have 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!"