Everything's Going Swimmingly?? Chapter 1
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I'm thanking G. Venereal. (George) for kindly editing my stories. He has as usual applied some 'gentle editing' to this story.
This will be turned into a TV cross dressing story. So if it is not your cup of tea you are well warned. I haven't decided what else I will include in the story. This is my first Transvestite cross dressing story. I could use some help from TVs and Cross dressers or anyone can help me please. Eventually at least S & M, B & D and maybe even some other surprises I can think of. barry97_97@yahoo.com
Now: "Every Things Going Swimmingly" Prologue
I was ready, bags all packed to head off to the University thanks for a Swimming Scholarship. It had been a long summer at the outside swimming pool. I had been lucky enough to get a job as the pool life guard for the summer. I stood in front of my bedroom mirror realizing how much my body had changed over the summer. I was a good six inches taller, slimmer, my blond hair was now a sun bleached blond. Lighter than it had been when I finished high school and a good three inches longer. I thought it looked super with my bright blue eyes. I had a more toned but slim tanned body than I had when I finished high school. I had also turned eighteen the week before. I finished packing and getting dressed in jeans and a T-shirt and headed down stairs.
"The summer passed way too fast." Mom had a hankie pressed to her nose mopping the tears from her eyes.
"Sandy isn't your baby any more." Dad said. "Stop with the crying. He'll be visiting for the holidays. He's only three hundred miles away. I told you, you could come to the train station to wish Sandy off."
"He's our only child, he'll always be my baby." Mom said continuing to wipe her eyes and blow her nose. "I don't want everyone to see me crying."
"Dad's right. I'm not a baby anymore mom." I said hugging her before following dad out the back door. I'll write to you mom."
"I still think you could be a wonderful clothes designer, but you're dad is forcing you to take Architecture. You're dress designs have been fantastic dear." Mom said.
"Leave the boy alone." Dad said. "I only want Sandy to get into a manly career. It was/is good enough for me. Why not Sandy. Dress designing is for fags."
"Don't listen to your father. I'm sure there are plenty of straight men dress designers. You're dad is just not using his head. I know you'll do well, so I don't need to give you instructions, how to get along at University. You've always been bright and eager. You'll make loads of friends. You've always been popular at school." Mom said kissing me on the cheek like I was a child going off to my first day of school, instead of heading for College.
Dad stuck his hand out the car window. "Good luck Sandy. Don't listen to your mother and her dress designing, it'll only cause you grief with the other boys at school. You kept your mouth shut with your friends here, so keep it that way." Dad said.
"If you say so dad." I said, turning and walking to the train station, not looking back.
I ended up with a seat to myself all the way. I thought about what mom and dad had talked about, since I finished high school. I had only told mom I wanted to be a fashion designer but she had to go and tell dad. Dad was upset with me and I ended up taking his advice and apply for architecture courses. When I got to the train station I caught the city bus heading to the University. I had done my homework about the city transit before leaving home.
The University was a far cry from high school. It seemed to dwarf my high school. I headed in the front doors looking for my dorm room. But then high school seemed to dwarf pubic school. My dream career was to be a fashion designer but I decided it was better to follow in dad's footsteps and become an architect. At least I'd still be designing, houses instead of women's clothes. If I was lucky I could also be a Y swimming and diving coach. Those and gymnastics were the sports I majored in. But dad was disappointed and blamed mom for not trying out for manly sports like football, basketball etc.
One thing for sure dad was really built and I admired his muscular body when he was wearing his gym clothes or baggy bathing suit. He said tight small bathing suits weren't his thing. Only boastful men and fags wore small tight bathing suits. I never did get to see his dick and that is what I'd always wanted to see. I figured it was a man thing to compare my dad's dick to mine. I wondered what I'd do with dad's dick as well. Maybe even suck it? Who knows!
I found my dorm and hoped I'd have a nice friendly roommate. I hadn't met him yet and this was to be the first time I ever had shared a room with someone else. I walked in my new room after unlocking it. It was empty except for an open suit case on the single bed closest to the window. I figured who ever was my roommate had already arrived claiming the bed by the window. There was at least four yards. separating our single beds. I placed my suit case on my bed opening it placing my clothes in neat piles on my bed. I was getting hungry by the time I had emptied my suit case placing all my things neatly on my bed. Except my good shoes and runners I put under the side of my bed. I didn't want to put my clothes and other things away until I found out what closet and dresser was mine. I looked at my watch remembering lunch was served in the cafeteria only between noon and one. I had the whole weekend before my first day of classes.
I walked in the cafeteria half full of young men around my age. Most looked to be in their late teens and early to mid twenties. I gathered they all had athletic scholarships for different sports. All the male students had good builds. I was told the University was an all male University. Across the city was an all female college. I had read the rules that indicated no females were allowed in the dorms. I didn't know the reasoning for that rule, after all I had considered myself an adult. Not that it mattered. I had to concentrate all my free time on my homework, swimming, diving and in the gym in high school. I hadn't had time for dating and wasn't particularly interested in girls. I enjoyed being around the guys working out in the gym, swimming and diving. I already missed my best buddy I hung our with since grade school.
Ben was always taller and more muscular than me, he was on the football team as a running back and I often watched him playing against other schools in our city. Ben would come to my swimming and diving competitions. I don't think he noticed how much taller I had grown over the summer but not gaining much weight. I was a lot more slim, my hair lighter from the sun with a golden tan. Even though Ben was a good six inches taller he had gained a lot more weight than I did and his was all muscle. He was a real hunk by the end of the summer. Since we we did different sports from each other I had never seen him nude. The least I'd ever seen him was in his loose fitting bathing suit. I have to say I liked looking at his muscular body but I always wondered what his cock and balls looked like, both soft and hard. Mine was just over seven inches not skinny or big around, I supposed it was just average.
I liked the guys I worked out with in the gym, swimming and diving. They had great muscular bodies and I often took peaks at their balls and dicks in the shower. I tossed it up to curiosity and most men compared their bodies, balls and cocks with each other. Although I have to admit I never saw any of them actually looking at each others cock and balls. I don't think they saw me looking at their bodies, cock and balls either.
I looked and joined the line up at the serving counter. My scholarship included food and board as well as tuition so I lined up. In front of me was a big guy that could have passed for Ben's twin as far as his body went. Ben had sandy hair and blue eyes with lighter hairy legs and chest. Under Ben's arms his hair was thick and darker than his head and legs. This guy had dark hair and hairy dark muscular legs while he was wearing shorts. He might have been of Italian or Greek nationality. I couldn't be sure only seeing him from the back. He sure had a broad back and I imagined a muscular chest and stomach. He had his arms and hands to his sides wearing a sleeveless white T-shirt so I could see his muscular dark brown, biceps. In other words he is a real hunk. I saw the side of his face when he turned picking up a tray putting it on the counter. I could see his dark brown eyes, square jaw and wondered if he was a football player.
I must have looked at the guy longer than I realized. The guy turned to me. "What the fuck you looking at?" He growled sounding angry. "What the fuck you doing here in the first place. This is an all male school. Females not allowed. Not that the guys wouldn't throw you a good fuck." He laughed. You're not half bad looking, except you haven't got any boobs. Shit you're not a girl you're one of those TV things."
"Excuse me but I'm not a TV. I happen to have a swimming, diving and gymnastic scholarship." I tried shouting, but it even I realized the way it came out, didn't sound very masculine.
"Glad you're not my roomy. I can't stand fags." The guy said.
I felt my face heating up all the guys staring at me. "I'm not a fag." I attempted to shout. "Maybe you're one."
That did it. The guy grabbed my T-shirt pulling me until I was face to face with his beet red face. "Who the fuck you calling a fag, homo?"
"Leave the fag alone Doug. I'm sure with no women for miles we'll find a good use for the fag." The guy standing on the other side of Doug said.
"Fine, you have a good point Stan." Doug said letting go of my T-shirt and shoving me back. I caught myself just in time from falling. "What's your name bitch."
"My name is Sandy, not bitch." I said keeping my voice down.
"Shit, it's even got a women's name. Sandy. Your parents must have thought you were a girl when they named you, bitch." Doug laughed.
"Sandy happens to be a boys name as well Doug and quit calling me bitch." I shouted.
"Bitch, bitch, bitch. What are you going to do about it bitch." Doug said.
I was too worked up to eat now so I dropped my tray back on the pile of trays and headed out of the cafeteria. I heard laughter as I walked out of the cafeteria. I could feel hot tears running down my cheeks as I walked down the hall heading for the elevator. When I got to my floor I ran to my room. I hoped my roommate hadn't come back while I was gone. I wanted to be alone. Thank goodness one thing went right my roommate wasn't in so I had he room to myself. I flopped on my bed unable to control my sobbing. This was the worse day of my life and it was only the first day of school.
I realized I had to control my crying before my roommate came in. I wiped my nose with Kleenex I had in my suit case sniffling. I was cold but sweating at the same time. I guess that's what was meant by a cold sweat.
I was finally pulling myself together when the door opened. I jumped not knowing who or what to expect. "Hello roomy." A guy in his early twenties walked in. He had short dark blond hair, around five-eight or nine, bright blue eyes, what I could see of him he had a good build. He was wearing baggy jeans and a loose fitting T-shirt.
"You're the guy the guys were picking on. Don't pay them any mind. Their just bullies. Not all the guys here are like Doug. Actually Stan isn't a bad guy once you get to know him. Sorry for my rudeness, my name is Kevin, Kevin Dolten." Kevin said walking to my bed and extending his hand.
"Glad to meet you Kevin, it's even better that we're going to be roommates." I said trying to smile. "I guess you know this is my first day."
"Yes, it takes some getting use to, being away from home for the first time. It is your first time being away from home isn't it.........?" Kevin said.
"Sorry I didn't introduce myself. My name is Sandy, it's also a boys name." I added.
"Yes, I know. One of my friends back home is named Sandy." Kevin said sitting beside his suitcase on his bed. "Glad to meet you Sandy. To bad the last campus girl, graduated last year. She could have helped you find yourself. I got to know her quite well. If you know what I mean. Wink wink. Her name was Paula.
"What are you talking about Kevin. I thought girls weren't allowed on campus? Did you and the other guys sneak Paula on the school grounds?" I asked.
"No, no. No one sneaked her in. At first she started wearing women's clothes. I was told the guys saved up so he/she could get implants. You know like real women getting implants, to make their breasts bigger. They're called silicone. They got their money back and even more when they prostituted her out to the guys in school. I paid for her a few times the last couple of years. Too bad she had to go and graduate. She was like a real girl except we fucked her ass. She always had her dick in a cage. Paula said once she started working she was going to save up to have the operation to make her a real woman. It's supposed to be expensive and students here couldn't afford to pay for the operation." Kevin said.
"What the heck are you talking about, you mean your Paula was a TV? I'm not a TV." I said.
"I know you're not a TV. Either was Paula when she started at the University. The guys had to teach him to be a girl. I gather she dressed in women's clothes in private, like you do. Did you bring any dresses with you?" Kevin asked. "You don't have to be embarrassed around me. I understand. The guys that knew Paula will understand and the new guys will grow to understand when they need some nooky. They like their girls to dress the part at least in public. Know what I mean?" Kevin winked.
"No I don't know what you mean. I don't wear dresses even in private. So stop winking at me. I'm not like, Paula, you're talking about." I said, feeling a bit confused.
"I was told neither did Paula when she started University. He/She thought he was a regular guy like you think you are. He/She thought he was Paul, but the guys straightened him out about that. Hehe. Get it straightened him out. More like gayed him out. He was told in no time he/she by then, was a screaming queen." Kevin said.
"Believe me that's not me." I said. "Get that out of your head. Let's talk about something else."
"Like what?" Kevin asked. "Sports. I mean real sports not fag things like swimming, diving and gymnastics. I mean baseball, soccer, hockey, football, sports like that."
"Wait a minute swimming, diving and gymnastics aren't fag sports. There are darn good men, real men swimmers, divers, gymnasts. So there!" I said, beginning to loose my temper.
"Yes I know. They're the ones that enjoy a beer or two, watching a good hockey, football, basketball game. You probably never watched, those sports. Have you?" Kevin asked.
"Well no but mom ruled the T.V., television that is, not TV as in he/she. Mom is real proud I'm a swimmer, diver and into gymnastics." I said.
"Yeah I bet she is, but what about your dad. I bet he doesn't go around bragging about you. Does he?" Kevin asked.
"Well, not exactly. But I'm sure he's proud of me just the same. Mom says he just doesn't show his true feelings of pride, like she does. What's that got to do with the junk you're talking about?" I asked.
"Everything. I guess I'll need help for you to realize what you really are Sandy. At least you won't have to change your name. You already have a girls name." Kevin said. "Lets talk about it another time. I have to unpack have a shower and get ready for the first day of school tomorrow."
"I have to unpack, shower and get ready for class tomorrow as well. Stop telling me all that junk, what I'm supposed to be. Besides there are plenty of guys named Sandy, like your friend for one and two Sandy Koufax. You going to tell me your friend and Sandy Koufax are pansies? He pitched twelve seasons, my dad told me for Brooklyn, L.A. Dodgers and is in the baseball hall of fame."
"That's true, but not every Sandy is like Sandy Koufax and my friend. You shouldn't go around claiming to be like my friend and Sandy Koufax. He was a true man, unlike you Sandy." Kevin said.
"Stop insinuating I'm not a true man. I am, so there." I said feeling flustered. "Go take your shower and leave me alone."
"You seem to think I'm picking on you. I'm not. I'm just doing my best to point out to you what you really are. Don't worry the guys told me it took a while to convince Paula who she really was as well. Speaking of taking a shower. Sure you don't want to come with me. Take a look at my goodies. I don't mind. After all you'll soon be dressing like a woman in public, not just in private." Kevin said, not sounding malicious. He actually sounding like he believed what he was telling me."
"No thanks, get out of here and go shower. I'll shower later." I said.
"Fine I know you want to have a peek. You haven't taken your eyes off my basket since I got in here and don't try to tell me you weren't looking." Kevin said grabbing his towel out of suit case. See you later Sandy."
"Yeah see you." I said as Kevin walked out of our room. I had to admit I had been wondering what his dick looked like. But weren't all men curious about other men's dicks? I wondered if other men wondered what a dick felt like in their mouths, like I did. I had a lot of weird ideas like maybe some guy pushing his dick up my ass. That was one of the weirdest ideas I had.
It seemed forever for Kevin to shower and wondered if he was jacking off. Now that would be nice to watch, I thought. I unpacked putting my clothes in the dresser drawers on my side of the room as well I hung up my shirts and pants. I finished unpacking. Kevin returned from the shower with a towel around his waist. "I'm nice and clean, do you want to start practicing on my dick?" Kevin said taking his towel from his waist. His thick cock bounced out slapping his wash-board stomach.
"Practice what?" I asked, but had a feeling Kevin meant for me to blow him.
"Blowing me of course. Some of us guys don't mind you're not dressed like a girl, but most will. Don't be shy come on over and get on your knees." Kevin said looking at me as if sucking his cock was supposed to be natural for me. I did like the looks of his cock which was drooling pre-cum.
"No way. I'm not down for that kind of stuff." I said, even though I would have loved to taste my first cock.
"In that case why are you licking your lips staring at my seven inch dick?" Kevin asked. "Answer me that. I told you, you don't have to be shy around me. A least with mine you get to practice before taking on the big cocks. At least work my balls with your tongue." "I'm sure some of Paula's things will fit you, especially her cock cage. No one will want to see your cock. The cage prevents you from getting hard when they fuck you. She took most of her dresses but did leave a few she got tired of. Your an inch or so taller than she is." Kevin said without taking a breath.
"I told you I'm not interested in dressing up. Mine is six inches and not half as big around as yours. You mean to tell me there are guys with bigger cocks than yours?" I asked.
"There sure are and you'll be enjoying them as soon as we have you wearing some of Paula's old dresses. As soon as we save enough you can buy some of your own. She left a load of make up as well. So at least you won't have to get make up. Your hair is a long enough to shape like a woman's as well. Never mind that for now, get down and work my cock. You said no to dressing up, but not to sucking my dick. Get down and I'll instruct you." Kevin said. "Be lucky your my roommate and not one of the tough black guys roommate's."
"What do you mean by that. The tough black guys?" I asked.
"You'll find out soon enough." Kevin said beginning to sound angry.
"Never mind all that shit, get on your knees in front of me and learn to suck cock." Kevin ordered.
"Yes Kevin!" Without thinking dropped to my knees in front of Kevin. "What do I do?" I asked!
"That's better. First you call me Master or Sir." Kevin said. "Next, ask me permission to lick my balls properly."
"May I lick your balls Sir." I said wondering why the hell I was letting my new roommate treat me like his slave.
"Permission granted GIRL." (emphasizing GIRL)Kevin said looking down at me with contempt.
I looked up at Kevin before looking at his balls, directly in front of me. They looked to be the size of two golf balls, wondering what to do next. "Don't call me girl, Kevin." I said feeling embarrassed by Kevin referring to me as a girl.
"Shut up." He said slapping my face. "Next time I'll paddle your ass. You didn't call me Sir and you are a girl from now on. Get used to it. Don't just look at them SANDRA, (emphasizing SANDRA) lick them. Go ahead and don't stop until they're soaking wet and I give you permission to stop. GIRL!" (emphasizing GIRL)
I didn't press the matter instead I looked up at Kevin sticking my tongue out and pressing it against his ball sack. I started to lick them. They weren't as bad tasting as I thought they'd be. I kept licking and licking taking them in my right hand kneeling flat on my lower legs under my ass.
Kevin continued looking down at me as I licked his balls. They were soon soaking wet with saliva. "That's good now take one of my balls in your mouth GIRL. Keep your teeth away from my balls.
I knew it would take some getting used to being called a girl and Sandra, from my new roommate. I wasn't about to contradict Kevin. I opened my mouth as wide as I could taking one of his golf ball size ball's in my mouth. I had no idea what to do next.
"Now carefully swish it from cheek to cheek." Kevin instructed in a less angry tone.
I looked up at him doing my best to swish his ball from one cheek to the other while keeping my teeth out of the way.
"Now the other one."
I spat out the first ball ready to take his other ball in my mouth. "Who told you to spit out my other ball. GIRL!" He said with a touch of anger in his voice, (emphasizing GIRL again)
"I'm sorry Sir. I'll try to do better." I said bowing my head looking at his feet. I raised my head looking up at him. "Permission to try again Sir."
"Go ahead. GIRL!" Kevin said emphasizing GIRL. "Take one ball first and then the other and shove them in each of your cheeks. You're even slower at learning than Paula was. Smarten up."
"Yes Sir. Maybe because Paula wanted to be a girl. I don't want to be a girl." I said looking up at Kevin's angry face.
"Neither did Paula at first, so shut the fuck up and do as your told. You have to get it through your thick skull you're a girl not a man." Kevin shouted sounding angry. "Get to work on my balls. NOW!" (Emphasizing NOW)
"Yes Sir." I said loud and clear before taking his left ball in my mouth pushing it to my right cheek. I did my best to keep his golf size ball in my cheek while taking his right ball in my mouth. Some how I forced it into my left cheek looking up at Kevin, wanting his approval.
"That's better now it's time for you to learn to suck dick. Spit out my balls first and wait for my instructions." Kevin snapped at me sounding annoyed.
I spat first one ball out before spitting the other ball out looking up into Kevin's brown eyes. "I'm ready Sir." I said.
"Good lick up the underside of my seven inch dick until you reach my cock head and pull it down with your hand." Kevin instructed.
I licked up the underside of his cock along the big tube sticking out. When I reached his mushroom shaped cock head drooling pre-cum I took a hold of it pulling it down. I was about to spit the pre-cum that ran in my mouth before pulling his cock down. "What the fuck do you think you're doing. Swallow my pre-cum, don't waste it. Anything coming out of another man, your to swallow. I do mean anything. Swallow what's in your mouth. GIRL!" Kevin ordered. "Don't forget to thank me.
I could taste his pre-cum sitting on my tongue. It didn't taste as bad as I had expected as I swallowed his pre-cum. "Thank you for allowing me to swallow your pre-cum Sir." I said.
"That's better now open your mouth wide I want to make sure you swallowed my pre-cum. Remember you're to swallow ANY thing I decide to put in your mouth." Kevin said. "When you have your mouth open stick out your tongue."
I opened my mouth as ordered, sticking out my tongue. Kevin leaned over looking in my mouth and to my horror he throated up phlegm from his throat and spat it in my mouth. I couldn't believe what he had just done and I was about to spit it out. I then remembered just in time. I closed my mouth holding my breath swallowing his phlegm. "Thank you Sir." I said after swallowing his phlegm.
"Have you eaten your own cum before?" Kevin asked.
"Are you kidding?" I asked. I had eaten my cum but didn't want Kevin to know I'd eaten my own cum before. I didn't want him to label me as fag. I wondered what another guys cum tasted like? Then it dawned on me, I had swallowed his pre-cum and phlegm and I was worried about him calling me a fag.
"Be Honest. I know you have. I can tell the way you're looking at me. I don't appreciate training a bitch that lies to me. So never lie to me.
"Okay I won't lie. I've eaten my own cum. I was curious how it tasted. That's the reason I ate it." I said.
"That's better. Like I said I don't want my trainee to lie to me. Take my cock head in your mouth. Watch your teeth." Kevin said. "Don't you dare scratch my cock with your teeth."
"I'll try." I said remembering in time to add. "Sir."
"You'll do more than try. GIRL!" Kevin said looking down at me and frowning.
I opened my mouth as wide as I could, stretching it wide open. I leaned forward taking his big cock head in my mouth. I pressed my lips around his cock shaft with his cock head in my mouth. I managed to keep my teeth from his cock. "Okay open your mouth slightly while I shove my cock in your mouth. SANDRA!" Kevin said. (emphasizing SANDRA) He took my head between his hands looking down at me. He pushed his cock further down my mouth causing me to choke when his cock head pressed against the back of my throat.
"You'll have to do better than that. Be lucky I'm horny and won't push you this time. Reach up with your hand and jack my cock next time I push my cock in your mouth."
I couldn't answer with his cock head in my mouth. Somehow I managed to take a deep breath through my nose. "At least you have enough sense how to breath with my cock in your mouth. Paula didn't the first time. Take another deep breath and let it all out and I'll shove my cock to the back of your mouth."
I took a deep breath in letting it out. Looking down in my eyes Kevin shoved his cock in my mouth not quite to the beginning of my throat. "Get jacking off my cock. SANDRA!" He ordered.
I raised my right hand doing my best to jack his cock. It was awkward jacking a cock the opposite way that I jacked off my own cock, but I did my best.
"That's the way keep that up and you'll soon be rewarded with my load, your first cum from someone else cock. Work my cock. That's the way faster."
I jacked Kevin's cock the best I could with his cock close to my throat. I couldn't breathe and I was afraid I'd die with Kevin's cock in my mouth. Thank goodness Kevin's breathing became labored and I knew he was getting close, at long last.
"That's it, that's it." He huffed and puffed. His cock grew thicker and longer, vibrating in my mouth. I knew he was shooting his load in my throat. He pulled his cock out until I managed to breath my mouth filling with his big load. "You got it all." He huffed and puffed pulling his cock out of my mouth. "Open your mouth and let me see my load on your tongue."
I opened my mouth carefully sticking my tongue out. "Close your mouth and swallow my load." Kevin answered.
I closed my mouth swallowing Kevin's salty, sweet load. "Thank you Sir." I said as soon as I swallowed his load.
"You did pretty good with your first lesson. I'll go down tomorrow, to my locker and bring up Paula's clothes, she left behind. Thank goodness these dresses were too big for her so they should fit you perfectly." Kevin said. "Go ahead and take your shower. You're finished for today. Don't think you're off the hook. You're real training starts tomorrow."
Any ideas from TVs and cross dressers. I'd appreciate your help. I'm thanking you in advance. barry97_97@yahoo.com