Pretty Boy by Gingerfred Man
Chapter One -- Too Pretty
What do you do when you're a boy and your genes made you pretty? Not handsome. Not boyishly cute. Pretty.
It wasn't bad when I was a small boy. My mother would dress me androgynously and everyone would compliment her on her beautiful daughter. Sometimes Mama would correct people. Mostly she wouldn't. When I was old enough to know what was happening, I was very embarrassed. I was a boy, after all. And I wanted to be a boy. I played with trucks and Army men and got into fights and played and followed baseball.
But it was difficult. I suspect Mama always wanted a daughter. Dad left her for the pizza delivery girl when I was around two. Fatherhood was too big a challenge for Dad. He couldn't deal with a kid when he was still one himself.
I was teased for my looks, of course. Some of the bullies in school saw me as an easy target. Until I rearranged some dentistry. I was no pushover and no wimp. Just pretty.
Thank goodness for Dennis Matthews, my best friend since sixth grade. Dennis was the one guy I knew who didn't care that I was pretty. He just treated me like Sam Burns, regular guy.
Not every male treated me with scorn, though scorn would have been better. There were a substantial number of males of all ages, who wanted to get me in the sack and do sex things to and with me. And I don't mean gay males. These were straight men in whom my looks and, I guess, personality triggered some deep, primeval instinct. They saw me, processed what they saw, and their instinct told them to get me into the sack.
I wanted none of that. I was heterosexual. They could just keep their stiffies zipped up.
I had no real girlfriends all the way through high school. And surprisingly, I didn't mind. Dennis had enough for the both of us. And a platoon more. Dennis and I were complete opposites. He was the most macho stud in school. I was considered a sissy. Just because of my looks.
Dennis and I were friends despite, or maybe because of our differences. I was always delighted to see Dennis. A little thrill gripped my heart when he looked at me. I got sort of tongue-tied when he praised me. Sometimes he would even bring me little presents. That's how friends act with each other, right?
As Dennis and I entered our senior year of high school, we celebrated our mutual 18th birthdays with pizza.
We were two days apart (I was older) and had just missed the cutoff, so we were the oldest kids in our class. I told Dennis that I was going to see about securing a girlfriend this year.
In his easy manner, Dennis said, "You don't secure girls, Sam. You woo them. Do you know how to woo girls?"
"Of course I do. No, I don't. How?"
"Listen to them. Girls love to talk. And complain. Nod and agree a lot, but only offer your opinion under threat of your life. Girls don't want to hear your opinion. They only want to vent." (How true. You are certainly an astute observer of the opposite sex)
Fascinating.
He went on. "Certain girls, probably the sexiest, you'll never get near because you don't have an eight-inch-diameter tattoo or even better, a Class C felony conviction. Most girls like the bad boys. They also like to be treated like shit, left pregnant, then abandoned."
Wow. "Why?" I asked.
"Regis himself couldn't answer that one, even with three lifelines, Sam. But remember, there are more of them than there are of us. Plus, some guys are gay, some don't want relationships, and some are too scared. The odds are with you."
As always, Dennis had made me feel better. And all funny inside too. Dennis knew so much about girls. I was proud that girls liked my friend. But maybe a little jealous too. I wondered why.
Chapter Two -- An Odd Mom
If you're reading this, you've probably read a lot of stories where a young crossdresser hides his appetites from the world, and especially his mother. I had a very different situation.
From the age of 13, I was encouraged by Mama to "try on some pretty things." We fought pitched battles over it. I wanted no part of girl's clothes, but Mama tried to convince me that it was best for me.
She was convinced that I was too pretty to be a man and would be unhappy as a man. She never insisted, but she pushed. Each year for Christmas and my birthday, she would buy me normal presents. But she would also give me several items of girlie things. Makeup toned for my coloring. Lingerie, skirts, shoes, tops, extraordinarily high heels. Panties and nighties were the most common gifts, along with sexual aids, which I'll tell you more about later.
All that five years worth of stuff was in a box buried deep in my closet. I couldn't throw it away. Mama would have my head. So I just pretended it wasn't there.
Of course we all have periods of curiosity. Now and then, over the years, I did pull out the odd nightie and try it on. It felt heavenly and when I looked at myself in the mirror, I looked as pretty as any girl I had ever seen. It was disgusting! In a strange, wonderful way.
A couple of times, trying to be nice to my mother, I modeled some of her presents for her. You know, the odd pink nightie or two. She was always so over the top with her praise of my beauty that I was beet-red with embarrassment. Sometimes the head of my tinkler was beet-red too from seeing myself like that. But I couldn't help that. So at around age 15, I refused to model any more.
Mama wasn't totally obnoxious about it, but I heard things like, "Oh, Sam, this 13-inch mini would look darling on you! You have such gorgeous legs."
I would cringe hearing stuff like that. But she was right. I did have gorgeous legs. I couldn't wear shorts in public. Seeing the legs that went with my pretty face would be way too much for the men of our town. They would either wank themselves into a dehydration coma or try and force sex on me. Yuck. Did I mention I also have an ass women would kill to have? A perfect bubble butt, plump and girlishly sexy.
Why me?
Chapter Three -- Phil
I've always heard that you never see the car that runs you over. I never saw Phil Winslow until he was deeply involved with Mama.
Mama was only twenty when she had me. So she was only 38 my senior year in high school. She was, by all accounts, a very beautiful and sexy woman. I knew that adults, even mothers have needs, so I never begrudged her her boyfriends. Until Phil.
Phil was good-looking; I'll give him that. But very arrogant. He was the first of Mama's boyfriends who seemed to be calling the shots. Mama liked that. And Phil was just enough of a bad boy to really appeal to Mama.
Mama was always very discreet about her men, until Phil. I'm sure she was getting her ashes hauled by someone or other over the years, but she kept it out of the house. Until Phil.
"You're a man now, Sam," she said to me one day. "I'm sure you'll understand if Phil and I express our affection for each other in our home."
I didn't understand. Why did Mama think it was all right to have screaming sex in the bedroom next to mine? I hadn't even really thought much about sex and had never even masturbated. Even when I was wearing those awful, silky nighties. Now sex was in my face.
Three or four nights a week, Phil and Mama would light up her bedroom all night. And they were loud. Mama was letting all her inhibitions go at once.
Of course I had to see Phil now and then. It was so embarrassing for me to know what I knew and know that he knew I knew it. But it didn't bother Phil. He spoke to me in a friendly enough manner. But I'm sure he knew I wanted him gone.
At least I thought I did. After about three weeks of my first second-hand experiences with carnality, the strangest things began to happen.
I began to get very excited by listening to my mother fucking her lover. My little willie was stiff the whole time I listened to them. I knew that you could make good things happen to yourself if you rubbed it. Even I knew that. So I sort of rubbed my cock and listened to them grunt and squeal and scream in orgasm.
It was wrong to fantasize about making love to my mother. Please. I knew that. That wasn't what I was doing at all. I'm embarrassed to tell you this, but I was imagining that Phil was making love to me, not Mama.
Sick, huh?
I couldn't explain it, but it was clear to me. I wanted to be under Phil, taking all of his hot cock into me. How did that happen? What kicked in with my chromosomes?
Oh. I was smothered by guilt. I was evil. I was cumming so hard I almost blew my head off.
Every night that Phil was with Mama, I would lie in bed and pleasure myself using the gayest, most evil, most vivid thoughts of Phil dominating me. Making me his sex toy. Making me cum over and over. I wanted to discuss it with someone who could help me stop. But I was even ashamed to tell Dennis. Even though I was sure he would understand. He was always so sweet and kind to me.
Worse, one afternoon alone, I opened the forbidden chest of girlie things in my closet with some intentions of trying out whatever I found. I wanted to find some things that might have made me more attractive to Phil. If he ever saw me in them. Which he would definitely not.
I was so depraved. Fighting my nature and my desires, I compromised. I took out only a pair of pink, nylon, bikini panties.
I was trembling when I stripped to the buff and tried them on. Ohhhhhhh. They were exquisite. They tortured and rubbed my hair-trigger cockhead and caressed my pretty pink ball bag. It was...I was.....Oh......That was the end of those pink panties. I came so hard that I fell to my knees. The panties were sopping with cum.
What was I doing? Had I lost it? I was through with this panty business. I was going to take a shower, get into proper boy's clothes, and go out and find a girlfriend. Right after I tried on those wispy, black thong panties with the lacy pouch for my cock and balls.
Oh, did they feel good. What would the girls in school think if they saw me like this? Their eyes always pass right over me. What would the boys think? I checked myself out in the mirror. Good golly! The boys would be attacking me in packs. They would be lined up around the block just to rub against me. I was H-O-T-T!
What would that no-good Phil think? I knew he was hot for Mama, but could he resist my forest-fire-hot body? No man could. I was irresistible. If Phil saw me he would run over and kiss me, making me weak with pleasure. He would stroke my pantied butt as he kissed my neck. He would take my clitty (did I say clitty?) between his thumb and fingers and twiddle the head, teasing me evilly, until I was gasping and then I would CUM! Just as I really was from the thought, ruining a second pair of sexy panties in seven minutes. Oh. It was intense!
Why was I so gaga over this gigolo? This loser? This bad boy? Why was I thinking about any man?
Three pair of cum-soaked panties later, I was no closer to an answer.
I washed the panties by hand and hid them in my closet to dry. I prayed Mama didn't find them and ask a lot of embarrassing questions, like, "So, what do you think about when you're tossing yourself off in your panties."
Mama would ask a question like that too. Believe me.
Thank goodness, I was undetected, but the next afternoon and every afternoon for three weeks, I was a slave to orgasm. I counted fifteen pairs of panties in my sissy chest and every one of them received several hot loads.
And so did my twelve pairs of sheer stockings.
I figured I might as well try them on too. I was glad I did, since the cool, sensuous feel of them rolling up my shaved legs made me cum even before I got my panties on. Cum would drool down my stockings and sometimes, very naughtily, I would lick it off my hand. I was becoming a cummy little tramp. In my own mind, at least.
Since I had already tried the panties and stockings, I figured it couldn't hurt to see what else was in my sissy chest. Mom had bought me lots of nasty little toys over the years. I held up what she had bought me on my thirteenth birthday. I was humiliated to receive it and it was still in the package. "The Cherry Popper," the label called it. It was a relatively short and slim, dark red, semi-hard-gel object shaped like a circumcised cock. It used batteries and vibrated when you turned a switch. The label said it was a "beginner's introduction to anal sex."
After five years without it, I decided that the device was just right for me to pop my cherry. I had never had anything in my tiny hole before, and the thought of even putting my fingers in there was scary -- and very exciting. I followed the label directions, lubricating it thoroughly. The five-year-old battery didn't work, so I found a new one.
Gently, I pushed the head against my tight sissyhole. I pushed again and gasped with pleasure as the head penetrated the fortress. It was wonderful. Even with that little, 12-year-old-size cock vibrating in my butt, I felt stuffed and sexy. I dared to stroke my cock as the little penis did its duty and built quickly to an orgasm. As I came, my ass clamped on the "Cherry Popper" and I wasn't spurting my cream! I panicked for an instant, then almost doubled over with the intensity of the delayed, strained ejaculation. Was this what anal sex was like? Oh my!
In a couple of days, the Cherry Popper seemed too tame for me, so I went back to the sissy chest. This time, I found the "Shower Buddy" that Mom had bought for me on my 14th birthday. It was a 50% bigger, semi-hard-gel cock, blue, angled strangely and attached to what appeared to be a large suction cup. I read the directions and took it to the shower with me. I used the suction cup to attach it to the shower wall tiles, then stripped and turned on the warm water. I soaped my body, and then shampooed my hair, lathering up really well. A lot of the lather, I applied to my little hole with two probing fingers. Then I backed into the well-placed Shower Buddy, inch by inch. Ohhhhhhh. It was incredible. I rocked back and forth on it, cumming twice, then a third, desperate time. I used the Shower Buddy so often that every time I went out in the rain, I got an erection
But there was more in that chest. I found my fifteenth birthday present, the "Tasty Boy." It was a big, seven-inch, lifelike, candy cock, intended only for sucking. How they did it, I'll never know, but every lick tasted like cum. Sweet, delicious cum. Mom had bought me a dozen of the Tasty Boys, and I licked four of them down to slivers that first week. My cocksucking technique advanced rapidly, but a warm, real one was what I wanted. Phil's.
I hoped that I hadn't tipped Phil off that I was spilling quarts of hot goo in his honor. I tried to act like a sullen teenager around him, as always. He couldn't tell what I was thinking, could he?
It got worse. I started to experiment with cosmetics. And the effect was startling. I went from pretty to the-cover-of-Glamour beautiful. The hetero part of me got stiff just looking in the mirror.
I began to wear panties to school. I couldn't be away from them.
I thought about wearing stockings to school too, but then it happened.
Chapter Four -- It
One Friday, I got home from school and saw a note from Mama: "Phil will be at the house at four. He and I are going out at four-thirty. Please let Phil in if I'm not home yet."
Rats! I was dreaming all day about cumming six or seven times right after school. Well, if they were going to be going out, I could prance around the house most of the night, cumming in every room. I laughed at that. I stopped laughing when I heard the bell. It was Phil.
I let him in. He greeted me semi-politely. I was sullen, while sneaking looks at him for details that I would use in that evening's fantasy entertainment.
I offered him a beer. He thanked me and took it.
Then the phone rang. It was Mama, asking to speak to Phil. They spoke. He hung up. I looked at Phil.
"Your mother's stuck at work. She won't be home for about an hour."
OK. I would just go to my room.
But Phil said, "You're different, aren't you? I mean you try to act like a nasty teenager, but you're not. You're a nice kid."
How did he know that? I blinked.
"Your mother adores you, you know. But she thinks you're different too. Of course, she can't see in you what I see."
I was trembling. I had to know. "What do you see?"
"Pure lust. You're one of the horniest people I've ever seen. And it's much more than just being a teenager. You have sexual needs."
Oh. I didn't like the way this was going. But my poor stiffie was rock hard. "You're wrong," I gasped.
"I don't think so. In fact, I think you're hard in your panties right now."
Oh no! What did he know? I felt as if I would cry. I wanted to deny it, but I couldn't.
Phil said, "Let me see your panties."
I stood at the edge of the cliff. I pulled back. "But I don't have any...."
Phil knew better. "Let me see your panties," he insisted.
I started crying. He didn't move to comfort me. He just stood there, waiting for my inevitable compliance. He knew I wanted him to see my panties more than anything. How did he know?
I sniffled, but unbuckled my belt. Then I undid and unzipped my pants. He sat down in an easy chair, as if to watch the show. I eased my trousers over my hips, revealing a flash of pink. I looked at him to see if that was enough. It wasn't.
I pulled my trousers down to my thighs, then to my knees.
Phil said, "Step out of the trousers."
No "please." Just, do it. My cock was throbbing and standing sentry-straight.
"Now the shirt."
He was a beast. What did he expect? What was he going to do? I was in his power. Oh my, was I excited!
I stood before Phil in my panties, shoes and socks. Trembling. Hot and bothered.
"Off with the shoes and socks."
Oh, no. He would see my painted toenails! I was almost peeing myself in fear. And excitement. I did as he asked.
He didn't act surprised or smug or anything when he saw my pretty toenails. He just said, "You're very beautiful."
I was standing there almost nude in front of a lusting, unpredictable man, who could ruin my reputation and maybe my life. But all I thought of at that moment was that compliment. He thought I was beautiful.
My cock was outrageous.
"Come here," Phil said.
I did.
"Don't be afraid. Sit on my lap."
Oh. I was almost fainting from excitement and fear and shame and delight. I sat on his lap.
Phil considered me.
"You could be a fashion model. You're a stunning beauty!"
I squirmed with pleasure. He hadn't even touched me and I was almost cumming.
Then Phil put his hand on my bare back and drew me toward him. I thought he was going to kiss me, but instead, he kissed my right nipple.
Electric shock! Shudder. Cum hard in panties. Tremble. Begin to cry.
"As I said, you have sexual needs," Phil repeated.
I was so humiliated, but I wanted him to pull my panties down, flip me on my stomach and pound his pork into my butt.
Instead, Phil kissed me. He kissed me for a good ten minutes. All the air left the room and I was gasping and panting. And kissing him back. I wanted him to pull out his cock and let me worship it with my mouth. But I could never have initiated that. He held my naked upper body in his arms and kissed me. Then he began to rub the front of my sopping panties. He didn't pull them down or reach in. He just rubbed. And rubbed. And I got bigger and harder. Still kissing. We did that for ten more glorious minutes and I began to feel another, bigger orgasm storming its way toward me. I flinched, I whimpered. I moaned. And I almost croaked when I heard my mother's car turn into the driveway. I wanted to run and hide, but my orgasm was almost there. Phil knew it too and he kept kissing and rubbing. Mama opened the garage door and began to pull in. I felt the first spurt of sticky cream leap into my drenched panties. Mama turned off her engine. The second spurt.
Mama opened the driver's door. The third spurt. She closed the driver's door. The fourth spurt and a rush of fear and adrenalin. Mama put her hand on the doorknob to the kitchen from the garage. Phil stopped kissing me and looked amused as I jumped up, scooped up my clothes, and tore upstairs. I ran to my room and just got in as I heard Mama sexily greet Phil. I peeked out of my door and saw her sit in his lap, right where I had been moments before.
I was jealous. How could I be jealous of my mother? But I was. And scared. Phil played a dangerous game with me and didn't flinch. Was I that brave? Had I made a wet spot that Mama was sitting in?
I was a mess. Especially in my sopping, sticky panties. But oh, baby, was I sexually excited. Phil wanted me!
Chapter Five - What I Thought I Wanted
Most of that night, I lay in my bed trembling in wild surmise.
What the heck had just happened? And even worse, what would happen next? At least a dozen times, I almost reached for the phone to call Dennis. But what would I have said? "Uh, Dennis, remember that Phil guy my Mama likes? Well he just kissed me and made me cum in my panties. Twice. And now I really want to suck his cock and have him fuck me.
That would have gone over well. Telling my best friend I was a simpering, cross-dressing faggot. Why didn't I just go up on the roof and jump off?
Well that no-good Phil was just going to get his tires rotated elsewhere, because that was it for me. No more sex with him or any male. No more dressing. I pulled the covers over my head and went to sleep.
I actually kept my promise to myself for the next week and, surprisingly, Phil seemed to notice and honor my new resolve. We treated each other as we usually did, which was mostly to ignore each other. Phil gave me no clue as to what he was thinking and that was just fine with me.
But my insides were burning. Having opened the box to my true nature, I found that the darned lid just wouldn't close. The following Friday, after Mama and Phil had gone out, I put on a pretty pink babydoll nightie that Mama had just bought for my 18th birthday. I looked completely edible!
Of course, after a week of abstinence, I was frothing at the mouth sexually. So I looked in the sissy chest for new friends. I found the "Anal Amigo" that Mama had given me for my 17th birthday. It was like the other fake stiffies, but with a key difference. When you had it fully inserted into your warm place, you pushed a button and the head and three inches of shaft pistoned in and out. Ohhhhhhhhhhhhh. It was rubbing on my prostate and I was in heaven. What made me think I could give that up?
The Anal Amigo took me to paradise five times that night and I fell asleep with it in my butt. My stomach was drenched with my own goo.
I awoke to hear Phil and Mama come in around midnight, then listened to them make tickles a little. But I fell back to sleep.
A warm, soft kiss and the feeling of a rough beard on my tender cheek awakened me
It was Phil! In bed with me! For some dumb reason, I looked at the clock -- 3:17 and pitch dark. What was he doing? What if Mama woke up?
But that kiss was all I really cared about, even though I was in my pink nightie, caked with dried cum, with my Anal Amigo under the covers with me.
Still, I gasped, "But, Mama."
"She's a heavy sleeper, Sam. Especially after sex."
True. Oh.
"Would you like to suck my cock, Sam?"
Oh, again. I nodded.
Phil lay back and showed me what he had. It was beautiful! Long, fat and uncut. With ridges and dark blue veins. And at that moment, very soft.
I inspected it carefully, including his long, wrinkled bag. I was shaking with fear and arousal. Then I got next to him on my knees and kissed the tip. He moved and groaned. Inexplicably, I giggled softly. I did enjoy giving a man pleasure.
He began to harden. I licked the tip, and then took the head in my mouth for a good sucking. But something was wrong; it didn't taste like the "Tasty Boy." I looked at it, then at Phil.
He gave me a wicked smile and said, "You're tasting your Mama's pussy, Baby."
That was when I knew that Phil was evil.
But at that moment, so was I. I resumed, swirling my wet tongue all around this bad man's velvet mushroom. I wanted his sticky cream and I was going to earn it. I soon had Phil moaning and writhing. Nature seemed to have made me a natural cocksucker too. At least Phil seemed to think so. After fifteen glorious minutes, Phil's balls contracted, his nipples erected, and he blasted his manly goo onto my pretty face. I was ecstatic! I had made a man cum -- given him pure joy. Phil looked at me. He considered kissing my cummy face, but just thanked me and left the room.
Was that how our relationship would be? Slam, bam, cum in your face, ma'am? Why did I want this loser anyway? I wasn't even really gay. Or whatever you call it when a guy is a girl and likes guys.
I had to steal him from Mama. How? Then how would Mama react? Was it worth it? My mind said no, but my genitals said yes, yes, yes.
Chapter Six -- The Week
Of course, the next morning I swore off Phil and sissying forever. I even made a point of eying down some babes at school. Not that they noticed. But Dennis did.
"What's going on with you, Sam?" Dennis asked. "You've been a bit whacked out lately. Now you're sizing up girls?"
"Yeah, so?" I said, petulantly.
"It's just a different you," he said. "And I'm your friend."
He was right. I managed a smile. "Sorry, Dennis. Maybe I finally reached puberty."
That broke the tension. I ached to tell Dennis, but my fear was enormous.
That night when I got home, I looked forward to a relaxing, non-Phil night.
Phil wasn't there, but it wasn't relaxing.
I kissed Mama. She smiled sweetly, but was troubled. Did she know I was sucking her man's cock?
No.
"I have to go away for training," Mama said. "For a week. Beginning Sunday."
That was in two days.
"I know you're 18, Sam, but you're still in high school and I don't want to leave you alone. How would you feel about Phil staying with you?"
All the air left my body. I turned many colors.
Mama innocently misinterpreted the signs as my anger.
"He would only be here in case you needed anything. He won't boss you or anything. It could be a way for the two of you to get to know each other."
Sweet goodness! There was no question of that. I gathered my wits and said, "OK, Mama. If he stays out of my way."
I went to my room, lay on my bed and considered the possibilities.
On Sunday, Mama said goodbye and Phil drove her to the airport. Should I be in a babydoll, stockings and heels when he came back? Would he want that? Would I?
I staggered up to my room for a good cry. When I entered, I saw a brand new pink baby doll with matching panties and stockings, laid out on my bed. And a note from Phil. "I'd love to see you in these. And make-up."
I shook with fear and excitement. He's going to fuck me tonight, I thought. And every night this week. I made a delicious little shiver of anticipation.
When Phil returned, I was in full babe mode. I wore Phil's gifts, adding a white garter belt and some pink, high-heeled mules. My make-up was stunning, accenting my now-welcome beauty to near perfection. Only my short hair diminished the effect. But very little.
I stood before him. A little virgin trembling before a big, hairy stud. Offering myself to him. Body and soul. He accepted.
Even Phil was moved by my beauty and innocence. On four-inch heels, I was nearly as tall as he. He kissed me, really seeming to enjoy it.
When he stopped, I said, "Thank you for the clothes."
He smiled. "You're welcome. No one ever looked better in a nightie."
I blushed. He was a flatterer too. Or I really was spectacular. I decided to believe him.
In my smallest voice, I asked, "Are you going to fuck me tonight?"
He laughed. Then got serious. "Do you want me to, Sam?"
I thought about it. "Yes," I said. Then remembered how big he was and got scared. But it was too late. And, I really did want his pork in my pooper.
"I never disappoint a beautiful woman. I'll fuck you tonight and every night this week, if you want. But one step at a time. Let's go upstairs and get on your mother's bed."
There was something evil about that too. And sexy.
I minced up the stairs in front of Phil, making sure he got a good look at my panties. He still hadn't seen my bottom or my privates. That was about to change.
He kissed me again, and then asked me to lie on the bed as he undressed. It was a great show, looking at his body unfold, and I was very hot, stiff and dripping, when he was totally naked. My panties were very crowded.
Phil looked at me, lying there in almost total submission and I began to be afraid. My mother wasn't even in the state to protect me from this, this man. With a big, hot drooling cock. What would I do if he were mean to me? Could I run? How far would I get running down my street in a pink nightie, panties and stockings? And how fast could I run in those heels. I was helpless to defend myself too. He was so big. And hairy. Did I mention that his cock was big, hot and drooling? Well, it was.
All I could do was submit to Phil's disgusting needs. You know what they are, girls. Cumming in our pretty bottoms. Cumming on our pretty faces. Cumming in our slurping mouths. Cumming on our feet and nipples and legs. Cumming.
So, I decided that was what I would do. You know, submit to him. So I just sort of lay there on my back, looking up at Phil submissively, with my arms in an "I give up!" pose.
He loved it. Any man would have. They all love to play "Slave Girl and the Emperor" and when we play along (as the slave girls) they go crazy for us. Tgirls have always known that. Genetic women know it, but couldn't care less.
Emperor Phil benevolently got next to his lowly slave girl and began kissing me. My panties got even more crowded. Then Phil reached in and extracted my stiff little dazzler. He seemed enchanted by it. Later, I guessed that it was the first cock Phil had ever held (other than his own). He rubbed my slick goo all around the head with his thumb and I was ready to play any game he wanted. He kept kissing my lips and rubbing my little dolly and the inevitable happened. I blew my sticky cream all over the imperial hand, whimpering and bucking with the staggering force of my rearranged guts.
The evening was going well as far as I was concerned, but it appeared my deflowering was imminent. I looked at Phil's big, hard thing. Then I touched my tiny hole. Something wasn't right with those proportions.
But Phil really seemed to want to disprove several laws of physics. He left me for a few seconds, re-entering the room with every pillow in the house. He put them on the bed, and then had me lay my stomach on them, so that my bottom was horribly exposed to the man with the big cock and the strong will. Ohhhhhh.
Phil rolled my panties down slowly, teasingly, to just below my sweet globes. He stopped for a few moments to say, "Sam, you have the sexiest ass I have ever seen on anyone. In person. In a picture. In my dreams, even. That is some ass!"
Of course I blushed. And maybe relaxed a little. Phil rubbed my cheeks, praising them and my beauty continually. I relaxed some more.
Phil then kissed my love pillows all over, making me squirm with pleasure. The bad boy even licked all over the insides of my bottom crack. Oooooh. Then he tongued my actual hole! Deeply! Double ooooooh.
By that time, I was ready to help him do that disgusting-needs stuff any way he wanted. But Phil wanted to ensure I had virtually no pain. So he got out a tube of K-Y jelly, put it on two fingers and slowly, achingly entered my anus, then rubbed the goo all over the inside canal of the only pussy I'll ever have.
I didn't know about Phil's disgusting needs, but that sure took care of one of mine. I fired cum like a jet engine. And screamed in orgasmic release.
Oh. Oh. Oh.
Wiggling, lubed fingers in the butt would make anyone cum until they were comatose. I was panting and gasping, thinking about what a hard cock would feel like after the hors d'ouevres were over. How could it feel any better than those two sweet wigglers that were onto my prostate and massaging it slowly and carefully? I wasn't even stiff and I was feeling hot rumblings. I looked over my shoulder at Phil and saw his expression. He was smiling and knew exactly what he was doing. Driving me insane with animal need. My poor limp doodle throbbed, quivered and drooled, not spurted, about another pint of sticky cream. My gut pulled. My balls vibrated. I was in sexual torment, then complete paradise. And I hadn't even been fucked yet.
That, apparently, was next. But Phil was tidy. He removed the two fingers from my ass and offered them to me for cleansing. I felt rectally empty, but Phil could have sent me on a one-way mission and I would have gone at that point. So I took those two raunchy fingers, soaked with lube and my ass juices into my mouth and sucked them sensuously. I don't even remember tasting them, so intense was my lust.
It was time. Phil rubbed my ass cheeks with his palms, got on his knees behind me, and presented his stiff, gorgeous meat for my deflowering. I began to weep, from both fear and need. He wedged his rammer between my cheeks and rubbed my anus with the wet tip. It was heavenly. And scary.
Phil pushed. The head popped in. I gave a little shriek and actually bit the pillow. It hurt a little. It was so big and I was so small. But I pushed back for more cock. Phil gave me all he had, slowly. Maddeningly slowly. But it didn't hurt. And that was a good thing.
So were the body-wide feelings I was getting from the first cock I had ever had in my ass. I was a girl at last. I was being adored as a sexual creature. And my pretty ass was being used for what it was designed for, a cock and cum receptacle.
Phil seemed to be enjoying himself very much. It felt good to please him. And each stroke on my tender prostate took me to never-never land. Was I going to cum again? <Gasp, pant, sob, whimper, choke> Yes, I was. And this one almost threw me off the earth's rotation. Every pore in my body exploded in orgasm. I sent out cum blasts that soaked through at least three pillows.
Phil grunted, "You are the hottest piece of ass I ever had!"
I felt proud. Then I felt squishy as Phil picked up the tempo and came, snorting and grunting, into my formerly virgin bottom.
Unlike most 18-year-olds, I knew what I wanted to be when I grew up. A buttfucked sissy. A frequently buttfucked sissy would be even better.
Well, I seemed to have made inroads to my ambition, because Phil was stunned with satisfaction when he finished my anal initiation.
Phil was not a tender man, but he took me into his big, strong arms and kissed and cuddled with me for a long time. I liked that a lot.
But I wanted more cock in my bottom. So I scooted away from Phil, got on my knees, and fondled his cock slowly and effectively.
Then (I was such a little tramp), I took Phil's big meat into my warm mouth and licked it all over. Phil may have been an old man -- at least 40! -- but his doodle sure got stiff when I did that. He had done so much work the last time that I decided to help him. I faced him, straddled his hips and slowly sat on his big boy. Mmmmmm. All the way down to the hairs.
I leaned over and kissed him with my lipsticked mouth. He liked that and put his tongue in my mouth. That excited me so much that I bounced on his lovepole as I tickled his ball bag. Bouncy. Bouncy. Yummy!
Phil responded by skinning my little clitty pole most deliciously. I came in less than five minutes, drenching Phil's right hand with the sweetest juice on earth. Phil grunted a lot, but held on until I made another sticky mess and an intense set of love spasms. That set off Phil's second go, which he told me was even better than the first.
As he kissed me, he told me I was a perfect angel of love. The flatterer. Of course I loved every word, because it was true. No man could have felt any other way about me that night.
Phil and I made love twice more that evening and I woke him up at three o'clock with a ball-busting blowjob. He liked that too. We had to go to school and work the next day, so I woke him up at 5:30 and had him fuck me on my back. I liked that the best. It was the deepest penetration and the greatest feeling of helpless girlishness. I'm not sure, but I think Phil was glad to get away from me. I believe the man was fucked out and needed to recharge.
Phil was in fine fettle that evening and night. He fucked me on my back; standing up, but bent over; spoon fashion; and on all fours. And I sucked his cock twice. Phil came six times. I made gooies fourteen times -- five times without even getting hard. Age eighteen is the sexual prime, you know.
How would I ever live without that? My asshole was the center of my thoughts and very existence. I wanted it stuffed with manly meat. And manly juices.
The third night, Phil fucked me twice when he got home early from work, then had me dress in a lovely little black dress he had bought for me. Phil had made reservations at a very chi chi restaurant and wanted to show me off. I was terrified, never having been dressed in public.
My fears melted when I saw how incredibly beautiful I looked in my dress, stockings and high-heeled sandals. Phil glowed with what I hoped was love. Or was I asking for too much?
Heads turned as we entered the restaurant. Male and female heads. Oh my. It was almost better than sex. If such a thing were possible. I already moved like a woman, tottering along on my five-inch heels. The absence of boobs made me look even more like a fashion model and my short hair accented my beauty.
It was a good thing I had given my little girl a tight tuck. She kept threatening to tent my skirts. All the admiration was getting to me and suddenly, in an amazing moment of clarity, I realized that I had options. Phil could have been one of thousands of potential admirers for me. Millions even. I began to think of Phil as the lucky one. More so than me. A good way for a girl to think, if she wants to make it through her life in one piece.
Still, Phil was the one paying for dinner and the one who would be cumming buckets into my aching pooper in an hour or two. So I flashed my 1,000-watt smile and giggled when he reached under my dress to stroke my bare thighs above my stockings.
Being en femme in public was a totally exhilarating experience that I hoped to repeat several times. Although it was not to happen that week.
As I was thanking Phil properly for the fourth time for buying me dinner, I realized that he was jealous. He didn't want to share me with anyone. Even to be ogled. Yet, he expected me to share my mother with him. Much to ponder.
Phil kept me home and fucked me most deliciously until Saturday morning, when he had to go to pick up Mama. I drained his balls so thoroughly the last time that I didn't think he would have much left for Mama. We girls are competitive, you know.
I decided not to wait for them to come home. I went over to see Dennis.
Dennis seemed delighted to see me, since I had been getting my bottom porked all week and didn't have a moment for him outside of school.
His parents had gone shopping, so we had the place to ourselves.
We talked about school and stuff and then Dennis asked, "What's been going on with you, Sam?"
Easy one. "I've been really busy, you know?"
"I've been your best friend forever. I think you should tell me whatever it is."
I looked at Dennis. I wanted to tell him. I couldn't. Then I did!
"No judgments, no telling?"
"That's always been us, you know that, Sam."
I began to cry. Inexplicably, I put my head on Dennis' chest. And even more inexplicably, he hugged and rocked me.
Softly, Dennis said, "It's OK, Sam. It's OK."
I felt so warm and protected in his arms. My sobbing eased and I said, "I know I look like a boy, but I'm really a girl."
Now, Dennis, who had seen my willie many times at gym and camp and stuff said nothing, but still held me in his strong arms.
I continued. "For a while now, I've been dressing as a girl, panties and such. And masturbating. Dreaming I was a girl and that a man was making love to me."
Dennis shifted in his seat a bit, but continued to hold me tenderly.
"I began to make love to a man two weeks ago and I loved it." I added quickly, "But I'm not gay. I'm a girl who likes men."
Dennis added two and two. "Phil?" Small hint of disdain at my choice in men.
I nodded. Dennis looked at me and then changed my life forever.
He kissed me. Softly. Lovingly. Thrillingly. Better than all my orgasms with Phil put together.
I was transported to Venus, the planet of love. But I wasn't even dressed as a girl. Dennis solved that little problem by removing every stitch of my drab, boy's clothing.
As he did so, he breathed to me, "I've always loved you. I couldn't admit it, even to myself. But I've always loved you. I've always thought of you as a girl, my girl, but how could I tell you?"
Then he began to kiss and lick my nipples as he stroked my overjoyed clitty. I had never been so happy. My true nature had been revealed to my true love and he not only accepted me, he was totally in love with me.
He worked me up into a frothy state. In minutes, I was cumming and screaming his wonderful name. I groped for his cock and devoured it with my hungry mouth. It was a great cock, attached to a fine young man. Who was this Phil guy anyway?
Dennis wasn't trying to dominate me. He wanted to love me. And I wanted to be loved. Although we girls do like a little dominance in the mix now and then too.
I fondled Dennis' hairy, heavy ball sack, then licked each round treasure until his eyes began to water. Dennis liked it very much. And so did his thick meat, which was leaking like the White House. Creamy pre-goo. Yummy, sticky semen. I licked and licked. Dennis threw his head back and gave me the biggest reward I could have ever wanted. All over my pretty, but un-girlied-up face.
We cooed and kissed and swore undying love. Then Dennis ate my ass for a good half hour, making me lose my girlie cream twice. I begged him to fuck me. BEGGED FOR IT! Oh, how that fired my boy up. He spooned up behind me, drove his big guy into me and moaned with joy. I squealed his name, then gooied yet again. Dennis was a superb lover, kissing me and rubbing my nipples with the copious cream that I had been avidly spilling in his honor.
When Dennis blew the biggest gusher of his life into my marvelous bottom, we both knew that nothing or no one would ever come between us. I would just tell that Phil character that he could stick his Johnson elsewhere.
I picked up my clothes and got dressed, kissing Dennis with the fervor of fresh, young love. We made litanies of promises to each other. Then I went home.
When I got home, Mama was sitting in the living room crying. I was reluctant to get too close to her, since I smelled like the men's room at a porno shop. But she seemed so pitiful, I hugged her and asked what was the matter.
"Phil is gone," she said. "He didn't even pick me up at the airport. He went to the airport all right, but got on a plane to go to his new job in California. It's all in his voicemail the coward just left me."
The utter rat! He was just using me for sex the last week he was in town. And I let him. Stupid, stupid, stupid. I decided to never hurt Mama by telling her about Phil and me.
I didn't think it was sour grapes when Mama said, "I don't know why I even bothered myself with Phil. He was hunky, but guys like him don't commit; they're just exercise."
Mama was right again. I stopped worrying about myself and comforted Mama. She may have noticed the smell, but didn't comment, except to say, "You're such a good boy, Sam. I'm so lucky to have you.'
I gulped and said. "But Mama, you've been right all along. I'm really a girl. And let me tell you all about why Dennis is very glad."
Please tell me what you think at gingerfred2005@yahoo.com
My other stories on nifty:
"Acting Up" transgender -- control "Panty Pleasures" transgender -- young friends "Woodville" transgender -- tv "Mothered" transgender -- control "Panty Town" transgender -- teen "Tradition" transgender -- teen "Punished" transgender -- high school "Panty Paradise" transgender -- teen "Kevin and Molly Go to Camp" -- transgender -- teen "Lovelife" -- transgender -- high school "My Three Sissies" -- transgender -- tv "Acting Out" -- transgender -- high school "Explorers" -- transgender -- high school "Pantied" -- transgender -- young friends "Rebuilding" -- transgender -- teen "The Au Pair" -- transgender -- surgery "Birthday Girl" -- transgender -- teen "Genes" -- transgender -- high school "Brothers in Panties" -- transgender -- teen "Coach" -- transgender -- control "Intervention" -- transgender -- high school "Winners" -- transgender -- teen "Teased" transgender -- high school "Irish Girls" transgender -- teen "Finished" -- transgender -- teen "Role Model" -- transgender -- high school "Freedom" -- transgender -- high school "Panty Fiesta" -- transgender -- control "Experiments" -- transgender college "One Fine Day" -- transgender -- teen "Stiff Resistance" -- transgender -- teen "Poker" -- transgender -- tv "Panty Sabbatical" -- transgender -- high school "Published" -- transgender -- tv "Stripped" -- transgender -- high school "Trained" -- transgender -- control "Something Better" -- transgender - tv "Fulfilled" -- transgender -- tv "Private Matters" -- transgender -- high school "Hard Times" -- transgender -- tv "Girl Nights" -- transgender -- control "Geography" -- transgender -- tv "Somewhere" -- transgender -- high school "Next Door Bride" -- transgender -- chemical (though I don't think it has chemicals) "Service" -- transgender -- tv "Test Driven" -- transgender -- tv "Sissy Stepmother" -- transgender -- tv "Slacker Moms" -- transgender -- tv "Sissies and the City" -- transgender -- tv "Paid in Full" -- transgender -- tv "Alternative Education" -- transgender -- control "The Boy Bride" -- transgender -- high school "Stiff Competition" -- transgender -- teen "Reservations" -- transgender -- tv "Panty Pride" -- transgender -- tv "The Panty Life" -- transgender -- tv "Super" -- transgender -- tv "Stocking Boys" -- transgender -- tv "Panty Secrets" -- transgender -- tv "Auntie's New Panties" -- transgender -- tv "Good Riddance" -- transgender -- tv "Generations" -- transgender -- tv "Fully Fashioned" -- transgender -- tv "Tommy's Summer Job" -- transgender -- tv "Tuition Assistance" -- transgender -- tv "Sweeties" -- transgender -- young friends