Underwood

I fondly remember my high school years. Classes were not particularly difficult and I had many friends. We used to go to parties, concerts, movies. My family was well to do and money was never an issue. As a result I didn't have to think about work or contribution to my family's income.

Young children liked me a lot. I guess I had good vibes with them. My neighbors asked me on occasions to babysit their little children, but most times I found a reasonable excuse to skip their request. As I said, I didn't need money, so why work?...

When I started my senior year, a new family moved to our neighborhood. The husband was a big burly man who seemed to have mood swings quite often. Pretty soon everybody tried to avoid him. His wife on the other hand was very gentle, nice and pretty. I liked her from the first time I laid my eyes on her.

In the first 2 weeks we barely said hello to each other. On the third week I met her on the street and she asked me, "I hate to bother you in the middle of the road, but one of the neighbors told me that you get along well with children. My boy is 3 and my daughter is almost 2 years old. I wonder if you'd agree to babysit them on certain evenings?"

"Lady, I'll be happy to do it. We were never officially introduced and I have no idea how to address you. Since you approached me, you may already know my name by now, but to be on the safe side, it is Bart Jonas."

She smiled and extended her small hand to me, "My name is Jane wood and my husband is Roger. The 2 children are Norton and Eileen."

"Nice to meet you ma'am. I am in my senior year and may be busy with assignments and exams, but I'll try my best to help you if you need me."

"Thank you. It's very nice of you".

Since that first meeting I saw her on several occasions in the local supermarket, library and even church. Most of the times she was by herself and soon we started chatting about all kind of subjects. The more times I was around her, the more fascinated with her I became. She was delicate, gentle, smiley. She was perfect!

Several weeks later I turned 18. A day after my birthday my parents reminded me that now as an adult they expected me to become more independent. I wasn't sure what all the implications were, but it was clear that using less money from the family savings for my personal fun was one of them. I thought to myself that from that time on, if other neighbors asked me to work for them, I'd do it - Cutting the lawn, tutoring their children and babysitting.

One day Jane saw me and asked if I'd be available next weekend to babysit their young children. I smiled and agreed even before she mentioned the amount of money I'd get. She came closer to me and thanked me profusely. Her fresh floral smell was amazing! I was in love...

The evening of the babysitting I arrived 15 minutes early to be introduced to the kids. The husband, whom I never talked to before, said hello with a smirk and his stare up and down my body felt uncomfortable. On the other hand, both children were nice and didn't seem to have a problem staying with a stranger. Jane caressed my hand and commented that she liked my instant bonding with her kids. The parents were going to a party and were expected to be back by 12 midnight.

I played with the kids for 1/2 an hour and then it was time for them to go to sleep. Neither one of them argued and 15 minutes later they were out. The time was 8:30 pm. I watched TV for an hour and then decided to check the fridge (Jane told me that if I became hungry, I could find there fruits and drinks). I grabbed a plum and decided to explore the rest of the house. It was an average size ranch style house with 4 bedrooms, 2 bathrooms, family room, living room, kitchen and a large basement.

The master bedroom was nicely decorated. In my mind Jane was responsible for the good taste it displayed. The beddings smell reminded me of Jane's scent when I met her on the street. I liked it a lot. I sat in their dark bedroom and thought about Jane. She was so much better than her gruff husband... She deserved much better. I wasn't sure whether it was the smell or simply thinking about her, but I became obsessed with Jane...

I went to check the drawers near the bed. The third one had her bras. Most were soft, 34B with variety of colors. They smelled terrific! Her panties were in the 4th drawer. Except for few high waist ones, the rest were low waist pretty ones. There was even a thong... Again, similar smell that intoxicated my mind.

Suddenly I got the urge to feel her underwear on my body and look in the mirror, imagining that it was HER... I watched the time. It was before 10 pm, so I still had 2 hours to kill. I undressed completely and gazed at myself in the mirror - My 5'6", 155 pounds looked good. More importantly, both Jane and I were fairly skinny, so I thought that wearing her underwear won't damage them.

I put on myself a pink bra. It felt nice on my skin. Having very little chest hair helped. Then I tried a pink low cut panties. The feeling was amazing! My dick barely fit inside the front. The panties friction with my pecker had an arousing effect and soon enough my prick found it's way to protrude above the waist. I became horny watching myself in the mirror, imagining that I was glancing at Jane in her underwear. I was ready to change the pink underwear with the thong, when I saw movement from the corner of my eye. It was Roger with his cellphone, videotaping me!...

He glanced at me with a mock smile, "What have we got here? Bart, are you a crossdresser? Do you like to dress in women's clothes?"

I was blushing and my body was shivering. I didn't know what to say. After a long moment I bent down a tried to collect my clothes and change, but he stopped me. "Not so fast young man. You look very pretty in my wife's underwear. Let's see how good you'd look when you put on a dress of hers too." He went to her closet and found a nice short red dress.

Roger chuckled, "You are a little boy, so I think it will fit you. Try it on."

I mumbled, "Please Roger, I don't want to do it. I want to wear my own clothes."

His stare became firm, "No Bart. If you want to dress like a woman, that is your chance. More importantly, I want to see you in it!"

What option did I have? Roger was bigger and much stronger than me. He also had me on his video camera in a compromising situation...

I tried my hardest and eventually managed to put the dress on, but it was very tight on my chest, flattening the soft bra.

"Oh boy, you start looking better, but we need to fix some details. You see, without breasts you won't be very attractive, so I'll bring you something to fill inside the bra."

He went to the bathroom and brought a bag of round cotton pads. He instructed me to insert them into the bra until my 'boobs' showed up. Once the bra was pushing forward making my chest looking like I was having C cups, he was satisfied.

He moved around, enjoying his new entertainment and commented, "Not bad, but some additions will be helpful. You need high heels shoes of course." Roger opened a closet and chose red 3" high heels, "These may be somewhat small on you, but I'd like it a lot if you still put them on."

My feet were much bigger, but seeing his threatening stare, I squeezed my poor feet into these shoes. I tried to stand up and almost fell forward. He chortled, "That's OK. You need some training, but with time you'll feel much better having on high heels."

I didn't understand what he meant by it, but I didn't want to give him any excuse to prolong my agony. Let him have his perverted fun and once it was done, I was going home and everything would be forgotten.

"Good. Now few more things and you are ready." He opened another drawer and pulled a blond wig, "Jane used it last Halloween. I think it will fit you well."

I struggled to adjust it until it expanded slightly and held in place. I looked at myself in the mirror. I didn't recognize myself!...

"Bart dear, not much more. I'll bring you the rest." He moved to the bathroom and came back with red lipstick, silver hoop earrings and nice pearl pin. "Here you go. Stand by the mirror and put everything on."

As I put the lipstick on my lips the best I could, I noticed Roger continuing to videotape me. "Roger, why do you take pictures? I was doing it for you and nobody else."

"Well Bart, I don't think you get the picture. You wanted to dress up as a woman with my wife's clothes. Without asking for our permission! You are hardly in a position to decide what comes next. The tape will stay with me for as long as I want and you are going to obey everything I tell you. Is it clear?"

I stuttered, "Whaaat do yooou want froom me?..."

He smirked, "I came home early, because Jane didn't take her warm coat. I caught you fumbling and then wearing her underwear and now everything else that is hers. Obviously you wish to be a woman! So I'll make you my bitch. First of all, you need to learn how to satisfy a real man in the bedroom, so my plan is to begin this evening with the basics. On your knees bitch!"

I gazed into his eyes, slowly grasping my dire situation.

"Look bitch, if you are not on your knees in front of me in 30 seconds, I'll make sure that copies of this video reach your parents, your teachers and all your classmates."

I didn't have another choice. I knelt in front of him.

"Good girl. Now unzip my pants and do it carefully!"

My fingers moved slowly and grabbed the zipper, lowering it cautiously all the way.

"Excellent. Now pull my hardening cock and caress it nicely. It will be your friend from now on."

My fingers grasped his expanding tool and pulled it out. His organ was big! It wasn't fully erect yet, but it was at least 6" already. It was circumcised with a large spongy head.

He grinned in my face, "Baby, you are doing so well, that you deserve a reward. And here it is, your new pacifier. Try it, I'm sure you'll like it."

I was disgusted thinking about putting it in my own mouth. It stunk... and I never had gay tendencies! Unfortunately, I didn't see any option but to comply. I spit on my palm, spread it over the head and then the shaft. Then I licked the mushroomed head. After getting over the initial odor, the taste was not revolting. I continued licking the shaft, noticing it engorging before my eyes. By the time it was erect it was about 8"!

I glanced at Roger's face. His stare was scary and his finger pointed to his pecker, "Time for a pleasurable blow job. By the time we are done here, you'll be a great cocksucker."

I bent down and gradually began to envelope his massive cock with my red lips. The head was larger than the shaft, but softer, so I was able to accommodate it in my mouth. The deeper I inserted it, the more it blocked my mouth. I tried to breath through my nose and push it in further until I started gagging. I pulled out and took a big breath. Roger grabbed me behind my head and forced feed me with his stiff member. He shoved it in forcefully and then let it stay there until my eyes filled with tears, my gagging became constant and large amount of saliva spilled from the corners of my lips. Then he pulled back slightly and seconds later penetrated deep again. He did it several times. My torture continued, but slowly my mouth seemed to enlarge and adjust to his huge girth. Minutes later my chin hit his hairy sac. He laughed, "You see bitch, you can do it. And with time you'll learn to love it as well. Now for your last assignment this evening. Suck me and be sure to use only your lips, tongue and palate. If your teeth hurt me, whether intentionally or not, you are a dead man."

It was my first time having a cock in my mouth. I didn't know if I was doing it right or not, but I made a valiant effort. Wanting to shorten the ordeal as much as I could, I gently massaged his testicles. He moaned and his cock jolted in my mouth. It felt like he was expanding further still. I gradually increased the speed of my bobbing and I felt his breathing quickening. His hands pulled the back of my neck into his groin. I heard a loud groan and he blurted, "Here it comes. Prepare to swallow!"

Seconds later ropes of oily salty liquid began hitting my back palate. I tried to back off, but his hands wouldn't let me. I almost choked. Eventually the flood stopped and I was able to swallow most of his spunk."

He held my neck for 2 more minutes, forcing me milk his last drops, before releasing his hands. His fingers turned off his phone - I didn't know he recorded the whole act!... "Girl, for a first timer you were doing good, but next time I expect improvement. Capisce? I need to go back to our party, but from now on you'll be available for my needs whenever I call you. One day I'll show you the whole recording and we'll enjoy it together. Starting this evening you'll be my bitch. Occasionally I may talk to you when Jane is around, But instead of Bart, I'll call you Underwood... Get it? Under Wood!..." He laughed loudly, very happy with his joke and my new nickname.

I removed Jane's stuff, while Roger took additional pictures. I was numb. I didn't know what to do. I just knew that I wanted out of this house as soon as possible. But I had to stay, because Roger was going back to the party and be back with Jane around midnight.

After he left, I sat in the living room, scared to death at what to expect when Roger arrived back with his wife. The TV was up with my favorite show, but my stare went blank.

Eventually they arrived. Jane said hello and went to the bedroom.

Roger stayed by me with a mock smile on his face, "Don't forget what I said!". As Jane reappeared, Roger rushed to the bathroom.

Jane smiled at me, "I hope you did not have any problems with the children."

"No, they were very good. I spent 1/2 an hour with them and then they went to sleep without arguments."

As Roger exited the bathroom and joined us, she handed me the money, "Bart, thank you for helping out. Can we count on you in other times we may need a babysitter?"

Before I could answer, her husband intervened, talking to Jane, "We just talked. He prefers that we address him by his middle name, Underwood."

She glanced at me, surprised by the name change, "I think that both names are nice. Is there a reason why the sudden change?"

I hesitated and Roger took the opportunity, "Jane dear, I need to show you some of the pictures I took with my camera. You'll be amazed..."

Afraid that Roger would show my photos in embarrassing poses, I said, "Roger is right. Please call me Underwood from now on."

"OK, Underwood, from now on I'll use your new name. Thank you again and good night."

...

A week later I got a text from Roger, "Underwood, next weekend Jane is leaving us to visit her sick mother. I'll be needing you here. During the day you'll take care of the children and once they go to sleep, you'll attend to MY needs. BTW, I have arranged a small closet especially for you in my garage. I even decorated it for you! Inside you'll find your evening clothes, as well as some 'other things', that will be useful. See you here at 10 am sharp."

He didn't bother asking if I was busy or not. It was a straight order. But I knew exactly what could happen if I didn't obey his command...

As told, by 10 am I knocked on the door. Roger opened with a smile, "Jane left 15 minutes ago. The children ate breakfast and they are bored. The outside weather is nice, so you can take them to the park around the corner. It has children's structures like ninja monkey bars and swings. They love it there, but they need constant supervision. I'll stay here. There is a good football game, that I'll be watching when you guys are out."

On one hand, I was somewhat upset that I was assigned to entertain the children when the father was watching TV. Then I realized that Roger could have used his freedom to abuse me, so being with the children was a minor inconvenience. I didn't recall Roger offering me money for my babysitting...

By 12 o'clock the kids were hungry and had to go to the bathroom. I returned back, took care of the bathroom issues and asked Roger about lunch. He was absorbed in his game and without looking at me he blurted, "Take them to McDonald's. You can buy them a happy meal and then bring me a Big Mac with French fries and a large coke. Tomorrow, before you leave, I'll repay you back."

The children were much more docile than I expected. They didn't scream, argue or cry. Both of these toddlers were nice and enjoyed their time in McDonald's. I made sure that the nuggets were cut small, nothing was too hot and no sharp objects were around. I actually began to like these kids...

We returned with their new toys and I put them to sleep for 2 hours, as per Jane's instructions. Once they fell asleep, Roger showed up and pulled me to the garage, "I want you to see your new closet. Here I'll keep all your stuff from now on."

It looked like a dresser with 2 shelves and a drawer. The door was decorated with stickers of Barbie and Cabbage Patch dolls! I guess Roger wanted to remind me of my feminine side... Inside I found a short straight bob hair wig, a pair of red 3" shoes that looked my size, 2 padded bras, 2 low cut panties, silk stocking, garter belt, a black short dress, a summery floral skirt, 2 blouses - one pink and the other one red. The drawer contained a small mirror, lipstick, small scissors and 2 additional kits - One for face treatment and the other one for extra hair removal. To my chagrin Roger seemed intent on making me be ready for him as a woman...

He gazed at me, expecting to hear me appreciate his efforts. I just nodded my head. His mood changed in an instant, "Bitch, you are not grateful enough to your master. Well, I'll change it soon, trust me. We have at least an hour before my kids wake up. You took the kids to eat at McDonald's. Did you give them any dessert?"

"I bought a chocolate chip cookie and gave each one half."

"Good! And did you get anything for yourself?"

"No. Why?"

"You treated them to something sweet and I thought that you deserve a treat too!" Subsequently he lowered his pants and underwear, exposing his long cock, "Here is a dessert for you. Enjoy sucking on it and as a special reward, toward the end you'll get to savor my special smoothie." He chuckled, happy with his own joke.

I knelt on the bare stone floor in front of Roger. The pungent smell of his genitals hit me immediately. I used my saliva to rub it over his cock and then his large sac before putting his pecker in my mouth. The smell was still disgusting, but somewhat milder. Again I gave him head, trying my best to harden him as fast as possible. If I was forced to blow him, let's make my suffering as short as possible. Either god or good fortune was on my side and 10 minutes later Roger ejaculated his spunk in my mouth. He lifted his pants back up and said, "Next time you better thank me for the free dessert!" and then he entered the house.

Later in the afternoon I played some games with the children. The father left the house without telling me where he went or when he'd return. However, he made it quite clear that I was expected to stay the night in their house. My prior experience taking care of toddlers was limited. I took the initiative, made small sandwiches with vegetables and orange juice before putting them in the tub and washing them. At 8:30 pm they were in bed. I read for them 2 stories and put them to sleep. Ten minutes later I got a phone call from Roger, "I leave the bar now. I'll be home by 9:15. Underwood, when I arrive, you turn into Liz, so use your new closet to dress up appropriately." Then he hung up.

I had mixed emotions. Last time when he made me look like a woman, I was scared and embarrassed. But the feeling of women's clothes on my body was very pleasant... If I was doing it in private and not to entertain Roger, I could have even enjoyed it!