Inside Out & Wrong Side Up

I was late again and this time it wasn't just by a couple of minutes. It was the third time in as many nights that I'd been stuck late at work but this had been the worst by far. There was nothing I could do really, I had to finish the project I was working on. I was already way behind schedule and if I didn't shape up I was bound to find myself out of a job.

None of that really mattered to Alex. She didn't even try to understand. If she said I was supposed to be somewhere at a certain time, I had to be there or else face the consequences. It was as simple as that. The funny thing is, no matter what kind of punishment Alex doled out I kept coming back. She had that kind of effect on me.

Alex is a beautiful woman by anybody's standards. She has a model's body with long, toned legs, slim hips, and a stomach you could bounce quarters off of. Her breasts are a touch on the small side but her firm, perfectly shaped ass more than compensates for her undersized chest. Last but not least is her beautiful face, with high cheekbones and cold, blue eyes, framed by dark hair that falls in waves down to the middle of her back.

I was the complete opposite of Alex. First was the matter of our age difference. I was forty-two while Alex was twenty-six, and where Alex was confident, self-assured, and demanding, I was quiet and unassuming. As far as physical appearance goes, I was nothing compared to Alex. I had the body and looks of an average male at best. I guess in some people's eyes I would be considered a nerd. I think that's where a lot of my insecurity comes from. I could never quite understand what a beautiful girl like Alex wanted with a man like me, but I figured I as long as she was interested I would do anything in my power not to lose her.

My relationship with Alex was strange to say the least. I'd never really had a girlfriend before, and to be honest, not that many girls had ever approached me. I'd always been self-conscious about my appearance and I was especially self-conscious about the size of my penis. On a good day it was barely four-inches long when I was fully erect. Alex however, seemed to revel in my inadequacy. She even went so far as to make me keep my entire body, including my pubic region, shaved. She liked to tease me by saying my baby smooth skin helped to show off my tiny cock.

I know she told her friends about my small package as well. Her friends would often snicker and make jokes about the size of my penis. Alex didn't really do anything to stop them either. In fact, sometimes she would be the ones making the jokes. Needless to say this caused further embarrassment and served to fuel my insecurity. Even with the endless ridicule though, I never considered leaving Alex.

Part of the problem was that I never really understood what my relationship with Alex was. I'd like to say she's my girlfriend. I certainly think I do the things that a typical boyfriend would do. I take care of her, bring her flowers, and buy her clothes. I basically do anything she wants. Somehow though I don't think she views me as her boyfriend. I know she dates other men and she doesn't really try to hide it.

I know because one time she let me take her out to this fancy nightclub. She left me all alone as she went off and flirted with every guy in the room. At the end of the night she picked out a "big stud," as she called him, to bring home with us. She made me watch as she let the "big stud" fuck her. She said she wanted me to watch a "real" man in action. I must say it was quite a sight. He simply hiked up her skirt, bent her over the back of the couch and pumped her. She was grunting and groaning the entire time, constantly admonishing the "big stud" to fuck her harder.

Rushing out of the office, I had no idea what was in store for me that night when I arrived at her apartment. By then I was more than an hour late and I was sure Alex wasn't going to be very happy. I finally walked in the door like a scared little puppy who knows he has done something wrong. Alex was sitting in her chair with the soft glow of candles illuminating the room. She had on a tight black bustier, a pair of tight, thong panties, garters with black stockings, and four-inch heels. She cracked a small whip across her open palm as I entered.

"I'm sorry, ma'am," was all I could whimper.

"Where have you've been?" she barked.

"I'm sorry, I had some things to finish up at work."

"I don't care."

"Yes, ma'am."

Right about then is when I noticed Sara sitting in a chair near the fireplace. Sara is Alex's friend. Attractive in her own way, Sara is about the same age as Alex, with a good body, and medium length sandy-blonde hair. She must have come straight from work as she was still dressed in a dark blue business suit. I was a little bit taken back by the arrangement and thought it was quite odd that Sara was there.

"You know Sara, right?"

"Yes ma'am."

"Sara just happened to drop by while I was waiting. I asked if she might want to stay and have a laugh at the expense of your itty bitty cock."

Horrified at the suggestion, I glanced toward Sara. She just smiled mischievously, quite obviously enjoying the scene.

"Take off your clothes."

I hesitated, not anxious to display my body in front of a strange woman, at least not in this situation.

"I said take off your clothes!"

"Yes, ma'am."

"Do it! Do it now!"

Realizing I had no choice, I did as I was told, and started removing my clothing piece by piece. I saved my pants for last, delaying the inevitable for as long as I could. It wasn't so much my small penis that I was afraid of Sara seeing. I'm sure she had already heard all the stories about it. What I was really embarrassed about was my underwear. Alex loves my feminine side and insists I wear tight fitting women's underwear. She says with my body shaved and my tiny little cock hidden tucked inside some hot panties I look like a little girl. She says that turns her on.

"Continue," Alex extolled.

After unbuckling my belt, I stepped out of my pants and now stood naked, save for a pair of pink panties, in the center of the room. Both women started to giggle at the sight. I remained frozen in place, unable to look at either of them.

"Sara wants to see your tiny, little pecker. She thinks little dicks are so cute. Go over and give her a good look at yours."

I walked across the room and stood directly in front of Sara. I took off the panties and gave Sara an eyeful of my "cute" little penis. I was already hard from all the attention. When my penis sprung from my panties and pointed at the ceiling, both women laughed with delight. I stared straight ahead as they did so, focused on the blank wall in front of me.

As I stood exposed, Alex rose from her chair and sauntered towards me, her hips swaying seductively. She stopped and stood beside me, giving me a good look up and down. When Alex was done staring she grabbed a leather collar from a nearby table. Reaching up, she fastened the collar tightly around my neck. On the front side of the collar was a metal D-ring. Alex quickly fastened a short leather leash to the collar. Sara watched with an amused look on her face.

"Down on all fours, bitch!" Alex snarled.

Trembling, I did as I was told and got into position.

SMACK!

Instantly, I felt the sting of her whip across my ass.

SMACK! SMACK!

Again her whip stung my ass.

"I told you not to be late. You should have been on your knees licking my ass an hour ago."

I was too stunned to respond. Alex had abused me before, but never to this degree, and certainly not in front of anybody else. But Alex seemed to get a charge out of humiliating with Sara watching, and Sara certainly seemed to be enjoying herself as well.

"Walk!"

Unable to do anything else, I began to crawl around the room on all fours. Both Alex and Sara giggled as I did so. After several minutes of this highly amusing behavior, at least from their point of view, Alex made me stop in the center of the room.

"Beg!"

I knew from before that this was a command to bring my hands up from the floor and remain on my knees. I did as instructed, with my tiny, rock hard cock pointing straight at the ceiling.

Alex soon reached forward and removed the leash. What a relief. It finally seemed like Alex had had her fun and was done torturing me, and the humiliation in front of Sara would soon stop. The only problem was Alex wasn't quite finished. She left the collar on and before I knew it she had my arms behind my back shackled in handcuffs.

"Wait here," she commanded before disappearing from the room.

I was dumbfounded once again. Why would Alex embarrass me in front of Sara like this, forcing me down on my knees with my hands cuffed behind my back. I mustered the courage to glance toward Sara. She was still sitting in a chair by the fireplace, but now she had her skirt hiked up over her hips and was lightly stroking her pussy through her panties. She smiled when she caught my eyes, intent on teasing me her sexy body.

Without warning Alex returned to the room. She still wore the bustier, stockings, and heels, but now her panties were missing. In their place was a strap-on dildo. Sara's eyes widened she saw Alex with a "cock." The dildo itself looked very realistic. It was flesh-toned with bulging veins, about six inches long and average in girth. Alex stopped in the doorway and gently stroked her "cock." It was quite a site to behold and probably one I'll never forget.

After teasing me for what seemed like forever, Alex slowly made her way toward me, stopping directly in front of me. She resumed stroking her "cock," her hands sliding up and down the length of the "shaft" positioned directly in front of me. She smiled as she looked toward Sara, who was now stroking her pussy more intently than before. Alex turned back to look down at me, on my knees in front of her on the floor.

"This is what a real cock looks like."

I stared from below as she continued stroking it.

"Do you like my cock?"

I failed to muster a response.

"You want to suck it, don't you?"

She took a step closer. Her "cock" was practically touching my lips. Once again, she turned toward Sara and smiled.

"And I bet Sara wants to see you suck it too."

Sara nodded, too excited to actually speak. Alex slowly moved the tip of her "cock" back and forth across my face and lips.

"Put it in your mouth. Suck it. You know you want it."

I did as I was told. I parted my lips and took her "cock" into my mouth. Slowly my lips ran back and forth along the length of her "shaft."

"Oh yeah, you like that don't you? You like to suck my cock I bet."

Alex was getting into it. Soon one hand was on the back of my head, driving my face deeper onto her "cock" as she thrust her hips forward to meet me. With every stroke I practically took the entire six inches into my mouth.

"Oh yeah, that's good. Show me you love it."

I began to whimper as she jammed her "cock" deep into my mouth. Alex was smiling with glee humiliating me. She clearly was enjoying putting on a show for Sara. Sara no doubt was enjoying it too. I'm sure it was a real turn-on for her, seeing a statuesque, twenty-something woman in a bustier and strap-on force feeding her "cock" into the mouth of a whimpering, forty-two year-old man on his knees.

With my hands shackled behind my back there wasn't much I could do as Alex took complete control. No longer was her hand on the back of my head simply guiding me, but Alex was now grabbing my hair to yank my head back and forth, forcing my mouth up and down the entire length of her "cock." I continued to whimper as Alex chided me.

"Oh yeah, that feels so good. Take it all in. Yeah, just like that. Show Sara how much you love it."

Alex slowed her pace somewhat and was now forcing my mouth to move in long slow strokes as Sara looked on. Sara's skirt in panties were now in a bunch on the floor. Her pussy was still partially obscured by her button-down blouse but you could clearly see a neatly trimmed patch of sandy blonde fur. Alex grinned as she watched Sara glide two fingers in and out of her pussy in perfect rhythm with the movement of my lips up and down Alex's "member."

"Sara likes watching you eat my cock, don't you Sara?"

"Oh, yes."

"I think she likes watching you take my cock deep down your throat. I think she likes watching you whimper like a little baby."

"Oh, yeah," Sara cooed as she continued to pleasure herself.

Suddenly Alex stopped. She pulled the hair on the back of my head and removed her "cock" from my mouth. I stared up at her, not knowing what to think.

"I bet you like it too. You like to suck my cock, don't you?"

Embarrassed and humiliated, I bowed my head.

"Yes ma'am."

Alex grabbed my head and forced me to look up at her.

"What did you say, I didn't hear you?"

"I said, yes ma'am."

Alex smiled mischievously as if she was satisfied and her proven her point. She looked at Sara who responded with a mutual grin of delight.

With the ordeal now seemingly at an end, Alex slowly circled me. After several passes she stopped and took off the handcuffs. I felt relieved that the ordeal was finally over. I had paid the price and would be sure never to be late again. The only problem was that Alex and Sara weren't quite through with me.

"Get down on all fours," Alex barked.

Quivering with fear but still unable to disobey her, I did as I was told. I was completely helpless, down on all fours with my ass up high while Alex stood directly behind stroking her six-inch "cock."

Alex moved in closer and began teasing and taunting me by lightly stroking my ass with her fingers. She continued with her taunts as she slowly slid the tip of her "cock" along the crack in my ass. Alex reveled in the power she had over me, treating me as nothing but a plaything, my body was hers to use however she desired. The fact that Sara was watching doubled her pleasure.

"I'm going to fuck you hard."

"Yes ma'am," I said almost as a reflex.

"Ask me nicely."

"Please ma'am, fuck me hard."

"Aren't you forgetting about our guest?"

"Yes ma'am, please fuck me really hard so Sara can watch."

"That's better."

Both women giggled at my humiliation.

Alex maneuvered into position, her "cock" in hand as it slowly split the crack in my ass. When the tip first touched my asshole, I let out a yelp. Alex didn't flinch. With her "cock" still wet from my mouth, she slowly guided it into my waiting hole. I whimpered as she drove the entire "shaft" deep into my backside. She grabbed my hips to brace herself in order to make sure she was in as deep as she could go. I grunted with each of her thrusts.

I closed my eyes in a vain attempt to avoid embarrassment. There was nothing I could do. If I didn't do exactly as Alex said I would surely lose her. So there I was, down on all fours with my tiny cock exposed, whimpering as Alex fucked me from behind. On top of that, she was letting her friend watch my complete and utter humiliation. I couldn't fathom how I let this happen. Why did I let Alex have complete control over me and my body? I couldn't help but imagine what would happen when it was over. I'm sure Alex and Sara would describe the episode in great detail to all their friends. In no time I'd probably have a room full of woman watching and waiting to take turns fucking me in the ass. To make matters worse, there wouldn't be anything I could do to stop it if that's what Alex really wanted.

As Alex fucked me, I was lost in a strange space between pain and pleasure. With my eyes still closed, Alex repeatedly slid her "cock" in and out of my ass. She went slowly at first, using long rhythmic strokes to invade me. Using my hips for balance, she buried her "cock" into me as deep as it would go. With every stroke my ass both relaxed and expanded and Alex's rhythm slowly changed with it.

Soon Alex was removing her "cock" very slowly and sensuously, only to ram it back in as hard and as fast as she could. Each time she grunted as her hips slammed against my ass. Each time I whimpered like a little girl.

It was all a show to Alex. Her pleasure came from dominating me, from seeing my ass high in the air as she filled it with her "cock." She delighted in my every whimper.

"You like to be fucked don't you? You like my cock up your ass."

"Yes ma'am," I cried as she grunted with another thrust.

Sara was clearly enjoying the scene. It seemed as if she was getting off solely on the sounds of our love. With her eyes rolled back in her head and legs spread wide, Sara was using two hands to pleasure herself. One hand was gently massing her clit, with the fingers of the other sliding slowly in and out of her hole.

"Show Sara how much you love it."

Upon hearing her name, Sara sprung back to life and opened her eyes to watch the action. Alex pumped me with abandon. I groaned loudly with each thrust. This seemed to spur both Alex and Sara on. Sara was now stroking herself furiously as she let out soft moans of intense pleasure. Alex continued to fuck me mercilessly, almost unaware that I was even there.

It was obvious that to Alex it was all about how everything looked. She wanted to put on a good show for Sara so they could laugh about the episode with their friends.

With my asshole sufficiently expanded Alex had free reign. She was pumping me like a fifty year-old man fucks his trophy wife. She hand one hand on her hip and the other on the small of my back. With each thrust she grunted with satisfaction and seemed to delight in watching my ass cheeks jiggle. The combination of my groaning and the obvious sounds of pleasure coming from Sara only seemed to excite Alex even more.

"I want you to make Sara cum," she extolled.

"Yes ma'am."

"Tell me how you want to be fucked."

"Fuck me harder ma'am. Please. Harder."

She did as I asked. I let out a sharp cry of pain with her thrust. Sara's breathing was increasing rapidly as she watched.

"You want it harder, don't you?"

"Yes, ma'am. Harder. Please, please."

Harder and faster Alex's "cock" slammed into me. Sara's pleasure was becoming more obvious. She was now grunting and moaning with every thrust, almost as if she was the one being fucked.

"You want to make Sara cum don't you?"

"Yes ma'am, please."

Every time Sara heard her name she seemed to take one step closer to orgasm.

"Are you going to make Sara cum?"

"Yes ma'am, please, just fuck me harder. Deeper. Please."

It was an obvious turn on for Sara, watching me being fucked solely for the purpose of making her cum. The sounds of me being abused were too much for her to take.

"Oh yeah. Take my cock. You love it, don't you?"

"Yes ma'am. Harder. Please."

"Are you going to make Sara cum?"

"Yes ma'am, please. Don't stop."

Alex pumped me furiously as I squealed like a stuck pig.

"Make her cum. I want to hear her cum."

Sara was nearing the point of no return. With her back arched, head relaxed, and eyes closed, her fingers worked furiously on her clit. She now seemed to be struggling to emit any sound at all. Her mouth was wide open as if she wanted to speak but no sound emerged.

"Are you going to cum, Sara?"

Sara opened her eyes long enough to take one last look at me down on the floor with a beautiful woman ramming a six-inch dildo in and out of my ass.

"Ooooooh. Yessss."

Spurred on by Sara, Alex slammed her cock into me deeper than I thought possible. Sara finger's worked hard and fast on her clit.

"I'm cumming. Oh God. I'm cumming," Sara screamed.

Alex didn't stop. She continued to pump me, grunting louder and louder with every thrust. Sara's orgasm seemed to last forever.

"Oh God. Oh my God. I'm cumming!"

Sara was screaming so loud I was sure the neighbors would hear but Alex didn't let up. She seemed to relish the orgasm she had caused and delighted in the fact that she had spurred it on with simple coaxing.