Underwood

I put on panties, bra, the floral skirt and a blouse. I adjusted the new brown wig on my head and tried on the shoes. They were too narrow, but felt much better than Jane's, that I wore last time. Then I took the lipstick and moved to the bathroom to put it on my lips. Without Roger around, I actually liked the way I appeared in the mirror. It wasn't perfect, but good enough for Roger. I chuckled thinking that I might surprise Roger next time by taking care of other minute details - Removing hair from visible places, putting more makeup on my face to mask my growing day's beard...

Roger entered the house and called me loudly, "Liz, where are you?"

I entered the living room and shushed him, "The children are asleep."

He just stood there and stared at me for awhile before announcing, "Liz, you are beautiful. I drank a little too much. Help me get undressed and into the shower."

It took me almost to an hour to remove his clothes, adjust the water temperature in the shower, wash him thoroughly and dry him. The good news - Now he smelled better...

He refused to wear anything and insisted that I'd take him to bed. Once there he pulled me in too. He blurted, "Liz, you were a great nanny. It's time to remove your clothes and join me for the night."

It was a king size bed, large enough for both of us. Well, I'd sleep in the same bed. He seemed too drunk to be dangerous...

I removed my feminine attire and slipped into the other side of the bed. Naked. I turned off the lights and prepared to sleep. But he grasped my hand and pulled me to him. Roger turned me, so his front was against my back. We spooned. I held my breath, hoping that he'd sleep soon. However, 2 minutes later I felt his cock hardening, pushing against my crack. I didn't react, still praying for a break.

Then I heard Roger whisper, "Liz, on Fridays I always have sex with my wife. She is not here now. You feel so soft and your bubble butt is very tempting... I think it's time you lost your cherry. And remember, even if it hurts a little in the beginning, I promise you that later on you'd love it!"

The man was crazy! Love it?!... I was fascinated by a woman. His wife! And now I was about to get penetrated anally... It sounded horrible, but I couldn't think of anything that would distract him from doing his thing. Obviously he wasn't drunk enough to vomit in the sink or fall asleep...

I stayed quiet, waiting to see, or rather feel, what he would do next. I heard him moving in bed, before his body touched mine again. He pulled my hand backwards and placed it on his shaft, making me bob it up and down along his engorged cock. Then his large hand smeared cold gel between my ass cheeks. After my initial surprise diminished, a finger poked my anus and invaded the puckered hole. Even though I guessed right what was Roger's intention, I wasn't ready mentally. My breathing stopped for a moment and my heart began racing.

He whispered again, "Liz, calm down. Everything is under control. As I said, first time may hurt a little when I penetrate your man-pussy, but if you don't fight it, you'll suffer much less!"

And then he shoved a second finger in my hole. His fingers started circling around inside my anal hole, probably aiming to enlarge it. After a couple of minutes my sphincter relaxed and I felt better. Roger's fingers were now sliding deeper, hitting my prostate and a wave of heat enveloped me. My dick began stiffening... What the heck?!... Slowly my arousal grew and my organ reached it's maximum size.

All of a sudden Roger pulled his fingers out. I didn't make a noise, but deep inside I hoped that he'd put them in again and continue his actions...

Then a larger, smoother, softer object was shoved carefully into my anus. It was definitely his giant cock. I didn't dare moving. I prayed to god, Jesus, Allah and even Buddha to protect my back side. As the huge thing advanced, I felt my sphincter stretch to the limit. At one point a sharp pain made me jolt forward. I told Roger that it was too painful. He pulled my body toward his and his palm rubbed additional liquid stuff on my bruised hole. Short time later the pain subsided and his pole was entering me one more time. It began hurting again. This time he held me tight and shoved his prick powerfully in. My pain was unbearable. My eyes were tearing nonstop and I heard myself crying. I was sure that my anus would never be the same again...

Roger hugged me and kept his prick inside my ass. Gradually my pain started diminishing and I stopped crying. Roger freed one hand and added more lube. And then he started moving very cautiously in and out of my butt. The pain decreased gradually. Although the pain was still there, a sensation of pleasure accompanied it. Slowly my pleasurable arousal intensified, while the pain decreased significantly.

Roger was aware of the way I felt and he started careful pounding of my bowels. The continuous massage of my anal canal, as well as my prostate took over and I became horny!... I had no idea what was happening to me, but I was on my way to a big orgasm. Now I was countering Roger's movements, helping him shove his monster even deeper.

As I was approaching my ultimate bliss, Roger pulled out. Hey, why?...

I whispered, "Please Roger, put it in again."

He blurted, "Liz, I told you that eventually you'd love to feel my cock in your cunt. Now if you beg NICELY, I'll be graceful and shove it in again..."

"Please sir, I wish to feel your beautiful cock in my man-pussy..."

"Good girl. And once we are done, you better thank me for taking care of your virginity!"

This time he didn't bother to be careful. His John invaded my enlarged anus. The strokes were increasing in power and speed as time moved on. After just 5 minutes my cock erupted forcefully like never before. It was amazing to climax without touching my own dick!

Roger continued pounding me for 10 more minutes before flooding my bowels with his own juices.

He fell sleep immediately after ejaculating. I went to the bathroom, emptied myself and showered before entering the bed again. It took me about an hour before I could sleep. My mind was on steroids - What happened to me? Am I gay now? My ass was violated by another guy! I even begged him to continue until I orgasmed too!!! What do I do next?!...

...

The next few days I could not concentrate on anything. Not in school, not when mom asked me to help her, not when I tried to go to sleep.

One day I met Jane near my house. She was happy to see me, "Underwood, I'll never forget how you saved us that evening. And now that I know I can trust you, I was thinking to use your services again. If you are available of course..."

"Jane, can you give me more details about it?"

"Sure. Roger has to fly to Mexico for several days. I promised a friend of mine to help her prepare for a big celebration Sunday afternoon for 6 hours, not realizing that it will be when Roger is away. I'll appreciate it if you can free yourself and of course I'll pay you handsomely for your trouble."

"Jane, I'll be happy to help you."

"Thank you. You are an angel..."

I blushed, "No, I am not."

She gave me one of her cutest smiles yet and went her way.

At home I was thinking about the babysitting job. I was very ambivalent about Roger, but he'd be out of the picture, so he won't be able to surprise me again. Spending 3 - 4 hours with her children was not a troublesome task. And then I'd have 2 hours for myself, likely to watch TV. Last time Jane handed me good money. It was 25% above the average pay for babysitting job in our neighborhood. So getting extra dough again would be a blessing...

I showed up at her house at 4 pm as promised. She was having on a baggy overall and an old shirt, ready to do whatever her friend needed. The kids remembered me and were happy to see me again. In the beginning we settled on the carpet and built a castle together. Then we painted and colored some pictures for their parents to hang on the fridge. I fed them based on Jane's instructions and added an extra soft candy that I brought from home. Jane did not asked me to do it, but I showered them anyway in the tub, letting them play with rubber ducks and a plastic boat. At 8:15 pm I put them to sleep after reading one of their favorite stories.

Ten minutes later I got a phone call from Jane, "Underwood, would you mind if I stay another hour and a half to finish everything here?"

"Jane, everything is under control around here. Don't worry, stay as much as you want."

"Thank you. You are a nice man and I like you..."

I mumbled, "I like you too."

She laughed and hung up the phone.

I was supposed to watch TV. But then it occurred to me that neither Roger nor Jane were in the house and nobody could bother me for at least one hour... I hesitated for few minutes before heading to the bedroom. I wanted to smell and feel Jane's clothes one more time...

I undressed and admired myself in the large mirror. Unlike some of my friends, I had no tendency to gain weight and my muscles were decent, even though I didn't do a lot of sports. Likely genetics played a role. I moved to the panties drawer and pulled the tiniest black one. I sniffed it. The scent was some mix of sea breeze, sweet fruit and Jane's perfume. Perfect! Next I explored the bras drawer. I picked a soft black one. It smelled just like the panties. I put both of them on. In the bathroom I found cotton pads and filled my bra with them. I watched myself in the mirror again. So far, so good. The lace panties touch over my dick felt so erotic... It started hardening and soon could not be contained inside the tiny panties. It protruded above the low waist and continued rising up. I searched other drawers and found a nude color silk stocking. I put them on too. Being almost the same sizes as Jane helped... Next I took the wig that I used last time and adjusted it on my head. Lastly I added the biggest size high heels shoes I could find and with a lot of effort fitted my feet inside. In the mirror, an attractive young woman in her underwear was staring at me. I added a short black dress that displayed ample cleavage - Even better! I needed lipstick and a touch of make up, but I looked good already! Jane's jewelry box was inside a closet in the bedroom. I selected a pretty silver necklace with a large red stone in the middle.

I felt awesome! I was a very attractive young woman. I trotted back and forth, swaying my hips, imagining young handsome guys behind me ogling my backside. Well, I was definitely looking sexy, but my bulging prick was something that I had to take care of, if I ever decided to go outside like that.

Suddenly I caught myself thinking about dressing up as a woman in public! It felt embarrassing and exciting... With the right planning, it was doable.

I had no desire to take off these pretty clothes, but it was late and Jane may show up any moment. I tried to put all pieces of clothing the way I found them, hoping that my own smell won't stay and reveal my secret.

I sat down and watched half a program of Seinfeld before Jane arrived. She looked tired, "Thank you again Underwood." She handed me the money and I left.

...

Two days later I was passing by and saw Jane working in her small garden. She wore a dirty-white tee shirt and short pants. Working in the hot sun made her sweat profusely. She bent down to remove the weeds and the upper part of her chest became visible. The wet shirt became transparent as well, revealing the swell of her tits pushing forward her soft bra underneath. I stood behind a tree and ogled her, every now and then rewarded by seeing the top part of her soft breasts peeking out...

While at home my first thought was that Roger the jerk did not deserve a perfect woman like Jane. I would give anything to be able to touch her once!...

...

Later in the week Roger texted me. "Underwood darling, I arrived home few hours ago. I missed your sexy body. Be here tomorrow evening at 6:30 pm, enter through the garage door (you'll find a remote garage opener in the second cactus pot on your right). Get dressed nicely to welcome me home as Liz. I'll be home around 7. The plan is to have fun while watching a nice movie."

That was new! I realized that Roger intended to use another opportunity when Jane was elsewhere to abuse my body, but doing it with a movie in the background?!... What the heck he had on his mind now?...

The next day I dressed as pretty as possible. I didn't want to upset him. I felt more at ease with his sexual advances, but I was still scared of him...

I put on the silk stockings, added more cotton balls inside my bra, made sure that the floral skirt was not wrinkled, checked my lipstick few times and then waited for him in the living room.

Roger arrived on time. He smirked at me, "Liz, I adore the way you look! You are such a sexy girl, that seeing you makes my prick jump up with joy and... anticipation. But first, let me put the movie on, so both of us can be entertained - Both physically and visually."

Once everything was ready and he only needed to push a button, he stood up and asked me politely to lower the silk stocking and the panties. I did it.

"Now stay between me and the TV, bend down and look at the screen in front of you."

He clearly wanted my ass. But why like that?!...

The reason was revealed once the movie started. It showed me, the only actor, standing naked in front of the mirror, fumbling in Jane's drawer, putting on a bra and panties, with my hard dick peeking skyward from above the panties waist band...

He laughed loudly, "Liz darling, I forgot to mention it to you, but after your first babysitting shenanigans, I installed a security camera in our bedroom. When I arrived back from Mexico, I watched the long recording. I saw Jane undressing a couple of times, but she does the same in front of me, so it wasn't so interesting. Then it captured you trying her underwear again. Lizzy, I do not get it, I bought you pretty clothes, why trying Jane's? Are you lesbian?!..."

I hesitated. Then a mumbled softly, "I like Jane's clothes. She is pretty and I like her scent..."

"But Lizzy honey, Jane is my wife! That is not nice to explore another woman's underwear, especially a married one. And thinking about it, she is MY wife! As a smart girl who did a stupid thing, you must understand that you deserve to be punished. Am I right?"

I was still bending forward with my rear in Roger's direction. I whispered, "I am sorry sir, I'll never do it again. I promise!..."

"Oh, cut it out! You were caught twice, so by definition you are a repeat offender! Well girly, be ready for the disciplinary action. And here it comes."

All of a sudden his palm smacked my butt cheek hard. It stung. I started crying.

"Lizzy, you better shut your mouth, before I change my mind and do it with a whip! Nine more of these 'gentle patting' and it will be over. Your tushie will be red for a couple of days, but you can take it. The good news - Once I'm done spanking you, I'll fuck your brains out..."

I was way more frightened of the spanking than invasion of my anus...

What can I say, Roger's large palms hit me hard for a total of 10 times. I pressed my lips together, hoping to survive the cruel assault on my vulnerable ass cheeks. Just before the last one, I was about to faint, so I knelt down.

He raised me on my feet, slapped me one more time and then blurted, "Liz, cheer up, now is the good part!"

I was wobbling on my feet. He held both sides of my waist and with one powerful shove inserted his pecker all the way into my bowels. I froze for a couple of seconds.

Then it dawned on me that Roger just tore my sphincter. Hurts like hell was too gentle an expression to describe my suffering. My legs gave up and I landed on the carpet with Roger's huge cock still stuck in me...

He was down too and whispered in my ear, "Yes Lizzy, it hurts in the beginning, but pretty soon you'll thank me!"

His brutal penetration without lubrication burned my anus like sitting on a fire! Roger ignored my agony and he began pounding my hurt hole as if nothing unusual happened. I couldn't react. My mind was numb. The only thing I cared about was for Roger to end this torment as soon as possible. At that point I hated his guts!

I was fortunate that he hadn't had sex for several days and 5 minutes later he ejaculated in my tunnel. Then he backed away and freed my lacerated ass.

I crawled to the bathroom, filled it with warm water and sat there for half an hour. Roger didn't bother me, which was great, but unexpected. I dried my butthole gingerly and while naked, I exited the bathroom. Roger was asleep on the bed, snoring loudly.

I sneaked out of the bedroom, put on my clothes as fast as I could and ran to my house. Nobody was home. I spread antibiotic paste on my hurting anus and went to sleep.

...

I am not sure if Roger ever told Jane about my sins, but I was no longer asked to babysit their children. A couple of times Jane saw me on the street. She smiled, nodded her head to say hello, but never again tried to talk to me.

In the year that followed, Roger found some free times and called me. Most times he made me suck his massive tool to completion, but on three other occasions he used my butthole. He never forced himself on me without lubrication again and his penetrations didn't hurt. In fact in two of these encounters I masturbated myself and climaxed as well...

Did I become officially gay now? Was it a manifestation of Stockholm syndrome?...

One day Roger called me and after damping his load down my throat, he notified me that they were moving to Phoenix. I was so used to dread his presence, that I couldn't believe my ears. Did I really hate him?!...

And then they were gone.

...

Fast forward 10 years.

I was married to a nice woman I met 5 years earlier and had 2 little sons. My wife Rita took a long break from her initial job as a supervisor in a local supermarket, to take care of my kids. I was a salesman in a Toyota place. We had many friends and life was comfortable. Our sex life became less exciting than in the first few months of marriage. Every now and then I recalled Roger and wondered what happened to him...

One day we were invited to a big Halloween party at a house of a good friend. He notified us, that he'd take care of the food and drinks, but unless we dress up in a way that nobody recognized us, he won't let us in... It was a joke, but the idea was that everybody wore a costume. Rita liked parties and she agreed to go with a big smile on her face.

She chose to be a one-eyed pirate. Then she smirked, "For you I suggest a different costume. Would you dare wearing a princess clothes?"

"Honey, where would I find the right costume?"

"Remember that four years ago I dressed up as Cinderella for a party with my workers? We are almost the same size, so you can try to use the same dress. Everything else we can improvise."

"Are you sure you want to see me in the party as a woman?"

"Of course dear. It will be funny and fun!"

"If you insist..."

On the day of the party I tried on Rita's white ruffle dress. It was slightly tight on my waist, but tolerable. I put on the silk stockings and red high heels shoes that I still kept in the garage from my times with Roger. Then Rita asked one of her friends to lend her one of her many long hair wigs. I shaved my face well and then added a touch of make up to make my lower face look more feminine. Lastly my wife helped me with a mascara and lipstick and then handed me her nicest necklace.

She stared at me before leaving the house and smirked. "Honey, you look so pretty. I am considering becoming a lesbian..."

At the party there were about 30 people. Everybody was into Halloween spirit. Some guests just put a mask on, while others invested a lot in a sophisticated attire. We chatted and drank and discussed and drank again...