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!
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...
Toward the end of the evening, our host announced that he wanted all of us to vote for the best costumes. Once everybody scribbled a name, the counting began. The majority votes went to Brian. He was a big, very manly guy, who dressed like a Templar. The number 2 vote getter was... me!
Brian was obviously under the influence. He was a rough guy even when sober, but now he was worse. He said, "I think that the 2 winners should have a celebratory dance together." Everybody started chanting, "Yes, dance together!"
Brian came toward me, bowed his head and mumbled. "Lady, will you give me the honor and dance with me."
I chuckled and gave him my hand, "With pleasure milord."
In spite of my high heels, he was taller than me by at least 5". He pulled me in his arms, leaned my head on his large chest and we began dancing to the music. Slowly other couples joined in on the floor.
At one point I felt Brian's hand caressing my back. I looked into his eyes and he whispered, "You are so pretty..." I whispered back, "Yes I am." He bent his head and mumbled in my ear, "Bart, I may be somewhat tipsy, but not completely drunk. If one day you'll really agree that you are pretty and I am handsome, we may have something to talk about..."
I stared at his face. He didn't flinch, "Bart, I am dead serious!"
I hesitated for a moment and then whispered, "Please call me Underwood..."
