Summer Vacation
(Authoress Note: All disclaimers regarding characters, age appropriateness etc. are in effect. I really advise anyone under 21 against reading my stories. This story is very nasty. Most will not like it but some will. Remember you don't have to read it. It takes a certain degree of maturity to enjoy this story. Do not write a review if you do not like the theme of the story. That is just childish. But criticism is always good and helps me.)
Chapter 1
(Please note I intentionally use both first person and third person voice for Chris and Crissy. Not sure it works but I thought it could be Freudian interesting.)
I was home alone. My mom and stepdad had gone away on a two-week cruise. My sister who was now a Senior in college was off with friends to Europe. And she no longer lived at home. She lived in an apartment, where she went to college, with three other seniors and so I rarely saw her except for Thanksgiving and Christmas. She didn't come home for summers, always having a job near college to make enough money to pay for the apartment.
I've always been effeminate. Often wondered why I was born a boy. At five foot five inches and weighing 123lbs I was the smallest in my junior year.
When I was seven years old a friend of my mother's sent me a birthday present. It was a t-shirt, white with the word "Crissy", in pink script, written in small font all over the shirt. Must have been at least a hundred plus "Chrissy."
My name is Chris. I was horrified when I opened the gift. My mother made me wear the shirt around the house and a few times under a regular button-down shirt when we went to church. We didn't have much money back then and mom said, `the lord provides.'
Mortified in church I wondered if anyone could see it. And at home when I passed a mirror wearing that girly shirt I wanted to cry.
I'm not sure what my mother was thinking but on Halloween she dressed me up as a girl wearing that shirt and a crinoline skirt, bobby socks and sneakers. She even made two pig tails with pink bows as well. She painted my lips with pink lipstick adding two very clownish red rouge cheeks. At seven you don't really disobey your mom. If you did, she'd take you over her knee and give you a spanking until you cried. If you screamed, squirmed or put your hand back, she'd make it worse. Also, you weren't allowed to touch your bottom after the spanking and had to stand in the corner bare ass, facing the wall, in an elongated time out.
She still does the same thing even though I'm in high school. I'm so conditioned I almost start crying at once. Sometimes I'm so nervous I've wet myself. It's so embarrassing. My sister would often watch and laugh. While I was facing the corner she'd come over and whisper in my ear, "Crissy you are such a sissy girl." I don't even remember if my sister was ever spanked.
We lived in a trailer park then. With little money I had to wear some of my sister's hand-me-downs. Such as her white cotton panties. The boys in the trailer park teased me all the time calling me, faggot, Princess Crissy, etc. I didn't know how they knew about Crissy, but I knew to slink away.
I went with my older sister trick or treating. Mom said she couldn't afford a costume, and this was the best she could do. My sister, four years older than I walked me door to door.
Of course, I had tried on my sister panties and bra when she was away at college. I liked the way they felt on my body, but I didn't think like a girl. I wasn't interested in boys. It was weird but only I knew.
When I was thirteen, just before my mom got married again and we moved, this one tough boy came up to me and asked, "would you like some gum?" I was so moved by his kindness I replied, "Yes please."
He told me to open my mouth and shut my eyes. Stupidly I did that and then he spat a wad of gum from his mouth into my mouth coated with his slime and nearly fully chewed up.
"Don't spit that out or I'll punch you," he mocked.
I went home crying.
When we moved, I was so happy. It was a small two-bedroom house. But there was another room up in the attic for me. My sister's room faces the street with a beautiful picture window with pink curtains. Her room joined a bathroom which I had to use as well. It was always filled with her girly stuff.
I would sniff her panties. Sometimes try her bra and panties on and imagine me as a girl. Not this Namby-pamby which I was.
When I was sixteen and my sister was off to college I often stayed in her room and sometimes I would wear a pair of her panties under my chinos to school. More and more I liked dressing as a girl. But I never thought about girl sex. Just the femininity of it and the silky feeling of the clothes.
By her senior year Sis no longer fit her teen clothing so she left all her clothes, shoes and even her old jewelry. Her ears were pierced now, and she had a whole new look. Whereas a teenager her clothes etc. were skimpy now she wore sweatshirts and some heavy metal rings and earrings. She even left her makeup since her style was more grunge now.
She teased me the day she was leaving saying, "Crissy you may like my makeup. Ha, you'll probably fit that dress in the closet. I leave you my wardrobe, make-up, perfume and accessories, enjoy yourself."
Most embarrassing but I thought it would be fun.
Over the next year my mom would chide me on my feminine look even commenting how I didn't need a razor since I couldn't grow a beard. To spite her I grew my hair shoulder length. How stupid of me. My stepdad sometimes would say how beautiful' I looked. Never manly.'
However, my parents took several weekend trips and I'd watch YouTube videos on applying makeup as well as how-to for walking in heels.
I was old enough now for my parents not to worry about me being alone. They had left a full refrigerator and a freezer with 14 mom-made dinners. Enough cash to buy more food. and the phone number of my Aunt Mary who lived almost 40 miles away, in case of an emergency. As if Aunt Mary would drive over since she's in her 80's.
They sent me a text each day to which I replied, "Everything is great. Just enjoy yourself." They didn't' call because the cost on the ship was prohibitive.
So, after they left this morning, I decided to see how girly I could look. Taking a warm relaxing bubble bath, I nervously shaved all the fuzz (well I didn't really have body hair except for some pubic hair.) For fun I even created a small landing patch. Wasn't much to look at since I'm naturally a light blond.
And you probably wonder why an effeminate boy like me would grow his ash-colored hair so girly long when not in a ponytail. Look I was always being picked on no matter what I did. Faggot, pussy, were names which came out in the school hallways every day. But enjoying dressing up when no one was around made it simple. So, I could even look more the part.
Maybe I had an abnormal balance of more estrogen than testosterone. When a doctor suggested testosterone shots my mother balked. First, she didn't believe in messing with "God's creation." Second, their cost was prohibitive. Sometimes I think Mom just liked me being her `girly boy.'
By noon, I was all dolled-up with all my sister's goodies left behind. There was a matching yellow satin bra and panties. I had even found some breast pads in the back of her closet she must have used when she was 14. She didn't have big breasts even now, so these pads filled the bra.
Her dressing table sat against the wall with a big mirror. So, as I sat down my back was to the window. I would learn later Sis had done this intentionally knowing the boy across the street had a crush on her.
I applied makeup, primer, color corrector, foundation, concealer, bronzer, highlighter, blush and then eyeshadow and eyebrows looked stunning. My green eyes sparkled. Earlier I had shampooed my hair and even used a curling iron from Mom's room to give my hair a little flip below the shoulders and a pretty ribbon flower hairclip. There was a box with Sis old jewelry. Teenage girl jewelry which she left. Cute gold tone clip on earrings. A few cheap rings which fit and a gold tone bracelet.
Then came the thigh high white stockings. Next, the little green dress Sis had claimed I would wear. Well, she was right. Last were heels. Sis called them pumps. I knew I could walk in them since I had practiced many times over the past year.
I stood up, looked in the full-length mirror attached to the closet door, and I smiled. I had thought about painting my fingernails but decided against it in case anyone came to the house.
Chapter 2
Across the street Mike and Jake were using Mike's dads telescope checking out the transformation occurring just a few yards away. Mike and Jake were juniors in college and home for summer break.
"I told you Chris was a pussy," Mike said.
"Yeah, he really is Crissy," Jake replied.
"Bet she'd suck us off,"
"You think?"
Listen, my dad's playing golf with your dad, they'll be gone for 4 hours of golf and another couple of hours of drinks and cigars.
"Yeah, well how does that get our dicks sucked?"
"My Dad has a key and the silent alarm code for their place. Crissy's Dad and mine swapped keys to keep an eye on things when one was away. I know where they are. So, we sneak over there. Go into her room snapping pictures on our phones. And then we tell her what the scoop is."
"Sounds like a plan."
"It's more than just a plan. If this works, we will be getting sucked off daily for the next two weeks we are here."
"Do you think it's gay to have him/her suck us off?'
"Nah, or would you rather pull on your meat for the next two weeks.
Mike, who is 6'2" and built like a linebacker went and got they key and code. Jake is 5'11". Just a tad chubby but solid. Like young men their age they both had scruffy full beards and similar brown hair and an abundance of testosterone.
Sniggering, they left Mike's house and crossed the street. Walking up to the door Mike inserted the key, turned the bolt, walked in, pressed the code on the keypad and proceeded towards the hall to Cris' big sister's room.
Chris, meanwhile, all dressed and Crissyfied was in the bathroom.
Mike and Jake entered the room with their phones out and ready.
I walked out of the bathroom, turned towards Mike and Jake, click, click, click, click.
In a state of shock, I stood frozen in place.
"Hi Crissy," Mike said.
In my best fem voice, I had practiced replied, "I'm not Crissy, I'm a cousin."
All the satin, makeup and heels couldn't put Chris back together again.
"We know who you are, and we are here with a proposition," Mike said.
"Well, less of a proposition than a demand," Jake chimed in.
In a way I felt uneasy, foreboding and yet femininely curious.
"What do you want?"
"Well, Jake replied, we both need a blow job or else we will use these photos or, we may just decide to use force."
Horrified, I looked at both these men. They were young, handsome, perhaps it was time to go a step further than dressing up. I even felt a tingle in my panties.
Both Mike and Jake, having planned this before, unzipped their flies and pulled their cocks out.
Crissy. me, stared in disbelief. Both their cocks made me realize mine was more a shrinking violet. Barely a third the size of Mike and Jake.
Dry raspy throat Crissy explained she had never done this before, but the men were undeterred. And before too long Crissy, crestfallen, had accepted her fate.
Chapter3
Here I was, Crissy, kneeling in front of two men with their cocks hanging in my face. I was about to crossover from crossdresser to cocksucker. I felt disgusted at this prospect but somewhere in the back of my brain was the realization this is what girls do.
She knelt in front of the men as if showing fealty but at the same time opening her mouth as a cocksucker.
Jake pulled my head towards his cock saying, "Girl get sucking and no teeth."
Mike snorted a laugh.
My lips touched the foreskin, and my nose smelled the testosterone. Fortunately, there was no nasty smell. He smelled soap clean. And so began my sissyhood.
Jake's cock entered my mouth. It was warm. He wasn't harsh with me but with his two hands held the back of my head he began to rock my head back and forth over his expanding cock. The girth filled my mouth and when the tip hit the back of my throat, I felt I was going to choke or gag. But then he moved my head back.
"You'll learn how to deep throat before too long. All girls do," Jake said.
It seemed like a long time and I felt him stiffen as he pulled my head towards his pubes. Then he paused and his cock pulsed as his jism filled my mouth with his seed. Although the thought said disgusting the taste wasn't.
As he pulled out, my mouth filled with his cum, Jake said, "Open your mouth and show me. Don't dribble any."
I turned my head up, opened my cum filled mouth, and as I looked up I heard the click, click, click of Mike's camera
"Swallow," Jake instructed.
As Jake's cum slithered down my throat and into my tummy Mike said, "Ok Crissy, one more cock to suck."
Mike's cock pushed past my lips, and I tried to sink into Crissy. Just a girl sucking a cock. It's what girls do.
He took his time, and my jaw and throat began to become sore. But before I could say anything Mike pulls his cock out and said for me to now suck his balls. They were very hairy, and some came off in my mouth as Mike jerked his dick.
"Crissy, open your eyes and look at me."
I looked up.
"Now Crissy do you know what every girl likes," Mike asked rhetorically?
"A facial," Jake chimed in.
And at that moment he began shooting his load all over my face. Gobs and gobs. Hitting my eyes, nose and lips. Some even landed in my hair. I turned my face towards Jake and saw him taking pictures. He had turned off the clicking sound, but I knew what he was doing.
"Crissy smile," Jake said.
And I did. All the facials I had girls smiling as man juice streamed on their faces. But even though I smiled, I couldn't figure out why any girl would smile.
Jake told me to keep my head tilted up and let the facial dry saying, "All girls rub it in to keep their skin looking young."
But at least I thought, it's over.
But it wasn't.
They both had me thank them and said I was to call them Mister Mike and Mister Jake.
As Mike's cum dried on my face and lips they told me they were home for the next two weeks and I'd be their cum slut. With the pictures I didn't have a choice but then again since I am very submissive by nature I wasn't as upset as most would have been.
"We will text you two hours before we are coming over or if we want you to come to here. You will do what you are told to do. And if you give us any sass or complain, he hesitated, well what happens to naughty girls who don't obey or complain?"
"They get punished," I answered.
"Yes, and how are naughty girls punished,"
I thought back to my mom spanking me and stuttered out, "They get a spanking?"
"Exactly."
"But tomorrow since my dad will be away for the weekend you will come over at 10am. Bring a bikini and a short summer outfit. No pants. Wear either a skirt or a dress. Make sure your finger and toes are polished and wear some sexy shoes."
And with that they left me with cum inside me and on me. I wanted to cry but as shameful as it sounds being wanted created some disturbing emotions.
My throat was so sore I went and got some Advil. Looking in the mirror I saw my dried cum covered face and messy hair.
Chapter 4
My parents were still texting me. Always around 8am my time. My sister had even texted me this morning with a photo of her with her friends and a few unknown guys. I noticed one of the guys had his hand on my sister's buttocks. I thought back to yesterday and wondered about girls giving blowjobs.
Shortly before my mom's text I got a text from Mike. Well now Mister Mike. It simply said, "Make sure you come over as Crissy. Be here at 10am."
I knew he meant I was to walk over there already in my `summer outfit.'
I went through my Kera's clothes. She had so many. I had planned to spend days wearing them alone. But now things had changed. She had three bikinis I chose this one.
I was having fun looking and everything fit. I wasn't thinking of sex. I was thinking how I liked being submissive yesterday. And I also enjoyed knowing the guys were turned on by me.
Giving a BJ wasn't a massive no-no. I guess it goes with the path I was on. So, I decided I was going to have some fun with this and see where it led me. Truth be told it was my first sexual encounter unless you count kissing sex. And that had been at a school dance two years ago.
This is the dress I decided to wear.
However, I was not fond of the facial. It was demeaning and made me wonder about women. Was this just submissive behavior or was it simply `pleasing their man?' How often does it happen outside of pornography?
There was no way I could fake breasts in the dress, but I had found some demi half-moon bra cups and tape which said they were waterproof. Sis had wrapped them in a towel with one of her bikinis. These were different from the others I had worn yesterday. These had some glue and the original product guide on how to apply them for swimming. I glued them on and wore them under the dress. Figured they could serve both in the water and out.
I knew Sis also had boxes in the basement and the small attic next to my room upstairs. I had planned to examine all this during my two weeks alone but now I would be examining them for a different outcome.
For those of you who are not effeminate you may find all this disgusting, but I had spent so much of my life thinking I was more girl than boy this excited me and scared me.
I applied nail polish to my fingers and my toes. A bright red to go with the lipstick. Spritzed one of her perfumes and I was ready to enjoy my effeminate brain and body.
Just before 10am I picked up the beach bag with my bikini, suntan lotion and other sundries and walked across the street with my head held high.
Chapter 5
Mike opened the door with Jake just behind Mike and they both looked at me with awe.
"Crissy, you look great," Mike said.
He held the door open and as I walked in, I said, "Good Morning Mr. Mike and Mr. Jake." I didn't use the last names. It just felt weird.
Mike told me to change into my bikini since we would hang by the pool.
While I was changing, I thought about how Mike side of the street homes were much nicer, and bigger, than my side. The street had a little boulevard between the two lanes with plantings but still, we looked out and saw what our future could hold. I laughed thinking do they look out with fear as to what their future may hold.
After hanging my dress up, taking off my sandals, putting on my sunglasses, well Kera's sunglasses (here's a pic of them) I walked out to the patio.
The boys were buff in their swimsuits and by this point I was all girl. Figured I'd have to give them BJs but so what. I was living my hidden dream but with sex.
I applied my suntan lotion and asked Mr. Mike to rub some on my back. He was more than happy to do so. And while he was rubbing some on my lower back, he slid his hand into my bikini bottom and his fingers cupped my ass. Then one finger slid down my crack till he reached my asshole. He began to push his finger in and I turned suddenly saying, "Oh, stop that Mr. Robb."
Strange, I felt excited, afraid and ashamed as he turned me around and kissed me on my lips. I didn't feel at all like Chris. I was Crissy.
Jake was in the house getting some sodas and as he opened the sliding glass door Mike (Mr. Robb) pulled away and smiled.
"I've got Cokes and Mountain Dew what do you want Crissy," Jake asked?
As I sunned, the boys (men) went swimming. They played Frisbee in the pool. The yard wasn't big, but it was nicely planted. Unlike the skimpy backyard we have.
Imagine, I didn't even think about tanning in a bikini. I was into being Crissy, a girl, and Mike had kissed me. It wasn't passionate but it wasn't a peck either.
Around 11:30 I asked if they wanted me to make lunch. Of course, they did and like the perfect little Susie Homemaker I went to the kitchen. Wasn't hard figuring out what to make. There was canned tuna, bread, mayo, onions.
When I came out to the patio with a tray I asked, "Who wants Tuna Fish Sandwiches and chips?"
We sat at the glass patio table eating, laughing, music was playing. The sun was shining and so was I.
About 12:15 the phone rang. Mike answered it and called Jake saying, "It's your dad."
Jake had to leave. Apparently, he had forgotten his chores and his dad had told him to come right home. He said he'd be back later in the afternoon.
Mike and I were alone.
Chapter 6
Mike and I swam. He kissed me again. This time with tongue. I was floating on air.
We went inside to shower and change. While I was in the shower Mike came in naked which led to love making (sex). He said I could call him Mike when we were alone and not to tell Jake about his kissing me and all.
Yes, he fucked me anally. And even though he used some Vaseline it hurt at first, I didn't complain. His rhythm and force got stronger until he finally came. I felt his cum inside me.
And that's when I knew who I was and who I would be for the rest of my life.
The End.