Competition

by Gingerfred Man

 

Chapter One

When I was thirteen, I never thought that I would become a simpering, man-pleasing sissy, sucking men’s big cocks and swallowing gallons of their cum. Taking their huge tools into my tiny bottomhole and milking their balls with my soft hands.

Not that there’s anything wrong with that.

I know it was mostly Mama’s fault. But I don’t blame her. If I didn’t want to tease and please men, I could have resisted. I hardly resisted at all.

It was really competition that made it all happen.

Mama and I only had each other. With my help, she ran a small hotel, the Acme, in a town where there were lots of oil workers and very few attractive women. Mama was such a beautiful, sexy woman, that lots of oil workers used our hotel just because they wanted to be near her.

The oil workers were big, rough, hairy men with calloused hands. I was only 13, but I could see that a lot of the men found their way to Mama’s bed. When Mama noticed that I had noticed, she said, "It’s marketing, Dennis. That Mrs. Harper and her trampy 16-year-old daughter Mary Ellen at the Zenith Hotel across the street are providing lots of physical ‘incentives’ to the guests. If we don’t compete, they’ll all stay over at her place and we’ll be in the poorhouse."

The poorhouse didn’t seem like a very nice place to me, so, as always, I went along with Mama.

My bedroom was next to Mama’s and I remember a lot of nights when I listened to her making strange noises and her bed squeaking. It would stop for a while, then start up again. Sometimes even in the middle of the night. And early in the morning. Mama always looked pretty happy after one of those "squeaky bed" nights. I remember too that for about five nights each month, our hotel’s occupancy often went down.

Around March of my eighth-grade year, right before my fourteenth birthday, I began to notice changes in my body. Strange changes. I wondered if it was related to those "allergy shots" Mama had been so thoughtfully giving me for about three months.

I asked Mama why my skin was getting softer, my waist narrower and my hips wider. But most of all, why my nipples were itchy and seemed to be puffing up. A lot. I almost had <blush> girl’s tiny breasts.

Mama said she wasn’t going to lose out to those rotten Harpers across the street.

But what did that have to do with my strange changes?

I remember that Mama wouldn’t let me get a haircut and it was getting really long. I had it tied up in a ponytail and for some reason, the guests, who always seemed to consider me an annoyance, started noticing me. Especially Carl.

Carl Haskins was one of Mama’s favorites. He would tease her and bring her little presents. Sometimes he would even take her out to dinner or a movie or something. Then he would bring her home and squeak her bed all night.

I couldn’t figure why Carl started noticing me.

As I ran around cleaning the rooms and changing sheets and stuff, I wore a really tight undershirt and a really loose sweatshirt over it to hide my breasts. But they kept growing.

I think Carl was the first to see that.

He began to bring me little presents. And he would touch me. In a nice way. My arm. My hair. One time I messed up and threw away some papers I thought Bill Kerns in room 4 was getting rid of and Bill got really mad at me. But Carl stepped in and protected me. I liked that too.

With my breasts growing, my center of balance was off and I started walking like a girl. I wanted to stop doing that, but couldn’t. Carl noticed. So did Bill. And the men in the other rooms.

I was in school a lot of the time, of course, and the men worked long shifts. But when they were around, they liked to drink and play cards in what we called the hotel’s lobby. Mama made good money from selling food and drinks and they tipped her well too. I was too young, but I served drinks too.

One May night, five months after I started with my "allergy shots," Mama said, "You know, Dennis, you could make better tips if you dressed a little better. Men tip attractive waitresses more."

I gulped. "But I’m a boy, Mama," I said. Of course, by then, that wasn’t so obvious. I had real titties. A solid B-cup and growing. And my body, except for my cute little willie, was like a teenage girl’s. A sexy, ripe, teenage girl.

"Dennis," she said, "it’s time you helped out in the war against the Harpers."

Huh?

Mama took me into her room and told me to strip. My eyes filled with tears. I didn’t want to show Mama my girlish body. I was ashamed of it. But you didn’t argue with Mama.

Mama seemed very pleased when I stood before her, naked as if I were about to shower. I trembled as Mama examined my hairless legs, pretty toes, smooth, heart-shaped butt and nice, tomato-sized titties. I shuddered when she caressed my nipples and my little three-inch cock was shamefully stiff.

Mama said, "I’m happy you can still get it up, Dennis. I was concerned that you wouldn’t. You’re much more attractive this way."

Attractive? To whom? And why?

"Let me just make sure everything is in order," she said.

Then Mama shamed me horribly! She took a little tube of petroleum jelly out, slicked up two of her pretty fingers, and slid them into my bottom hole. Agghhhh. I almost fainted from shame. And excitement. What was happening?

Then Mama made things worse. With her fingers still "back there," Mama touched my little cock with her other hand. I jerked, then began to cry with even greater shame.

But I know Mama loved me. She said, "It’s all right, Sweetie. I won’t hurt you. Don’t you like this?"

I did. Very much. That was why I was crying and ashamed. I whimpered at Mama.

"You really are a sissy! That’s good. Now Dennis, do you like this?"

Mama slid the long, wrinkled, brown skin from the pink crown of my little guy. I squealed. Oh. I was upset that it was a sissy thing to do. Mama smiled and persisted, running her sweet fingers in and out of my bottom as she ran my foreskin up and down. Up and down. Ohhhhhhh. My eyes got wide. I gasped and, panting with lust, I shot the first cummy burst of my life into Mama’s hand.

Mama said, "It’s OK, Baby. Good girl. Let it out. Good girl! Oh. So much cum. That was a nice one. Mmmmm. Very good, Sweetheart. You needed that, didn’t you? Very nice."

It felt as if my essence were leaving my body. I didn’t know what happened, but I liked it very much. But what was this "girl" stuff?

Mama hugged my naked body and said, "You’re perfect, Dennis. Pretty, sexy and feminine. And you cum like the Trevi Fountain. The guests will love you. And the Harpers will be in the poorhouse, not us."

I was beginning to understand what Mama expected. And it terrified me. But my cock was once again stiff as a triple martini.

Mama reached into a drawer and pulled out a delicate, wispy pair of pink panties. "Try these on, Sweetie," she said.

"But Mama, those are for girls."

I guess Mama figured by that time I should have caught on. She said, "Dennis, I think you know how difficult it is to make ends meet. We work hard and sometimes we have something to show for it and sometimes we don’t. You’ve been a great help to me, but you could help me a lot more and help yourself if you would just put yourself out a bit. I’m sure you know that I do little extras to keep things going."

Mama’s little extras made her bed squeak.

"Now no one’s asking you to do anything bad. Just make the hotel a little more attractive for the customers. How much do you usually make in tips on a night when the men are playing cards?"

"About ten dollars, Mama. You know. I give it to you."

"Would you like to earn a lot more than that?"

"Not if I have to do……bad things."

Mama laughed. "I’m not asking for that. Now put the panties on."

What choice did I have? I put the panties on.

Oh my goodness. They felt wonderful! Cool and light. And very pretty. They made my bottom look very cute. And they caressed my little doodle and balls very sweetly.

Mama said, "Look at yourself in the mirror. What do you see?"

In my panties and nice titties, I……..

"You look like a girl, Sweetie."

Mama was right. I was so ashamed.

"Don’t worry," she said. "No skirts and stockings yet."

Yet?

Mama said, "Put the tight tshirt and loose sweatshirt on again. I know that’s how you’ve been hiding."

Sniffling, I put them on. I didn’t look as girlish, but I was very cute.

"Now these shorts, Dennis."

They were very brief. And light blue.

My legs were hairless. With my sweatshirt and my hair in a ponytail, I looked like a girl on her way back from the beach. Mama completed the effect by painting my toenails with a clear polish and giving me a pair of flat, backless sandals that exposed my pretty feet and toes.

I was mortified. Where did she expect me to go dressed like that?

"The men’s poker game starts in ten minutes. You’d better set up."

Noooooooo. I couldn’t let the men see me like that. They would tease me and call me a little faggot. Maybe even beat me up. "Please, Mama. No."

"Dennis, I think you will be very surprised and even happy. Now go out there and serve the drinks."

Would I survive the evening? I trembled with fear and shame.

 

 

Chapter Two – The Poker Game

Since it was Saturday night, the poker game would be a long and boozy one. Mama and I were very busy making sandwiches and serving drinks. A lot of our income came from those games.

I stood behind the bar where no one could see my legs and toes. And girlie shoes.

I prayed I could hide back there all night. The guys were about an hour into their game when Carl yelled back to me to bring him a Four Roses (cheap whisky) and an Iron City (a beer, for you non-Pennsylvanians). I had to do it.

The shoes made we wobble and wiggle more than I wanted to and my new titties affected my balance, so I guess I was walking pretty girlishly when I gave Carl his shot and beer chaser. I sissied away, hoping he wouldn’t notice me. But I did feel hot stares from the six men, though I couldn’t tell which ones. A couple of minutes later, Carl asked me to bring him a ham sandwich. Mama and I made excellent sandwiches and the guys ate them up at $5 a pop. I brought the sandwich to Carl and started to leave, but I felt his hand on my arm.

"Stand next to me, Dennis. You bring me luck." And he gave me $10. Wow! That was usually what I made working the whole night.

I stood next to Carl, hoping that no one had noticed Mama’s enhancements of me. Carl won a hand. Then the next. And the guys began to joke about me being lucky for Carl. Then he gave me another $10! Wow!

Then I felt his hand on the back of my thigh.

Carl had me stand to his left. When he wasn’t dealing, he could play right-handed and touch me left-handed. That was a lot of touching.

His hand was warm, but very rough. He was gentle when he rubbed me and it felt very good.

But oh, it was horrible. Was Carl gay? Was I? Why was he rubbing his rough hands along my smooth thighs? Why was my little willie as stiff as concrete? And tenting my shorts?

Had the others noticed? They gave no sign. Bill asked for a sandwich and to fetch it, I disengaged myself from Carl, who acted indifferent to me leaving.

Then Bill gave me a $10 tip and asked me to stand next to him for luck. Carl joked about everybody getting lucky with Dennis and everyone laughed. Except me. Bill was stroking my knee and I was getting all hot and bothered. My erection was tenting my short shorts and I was sure everyone could see. But no one said anything.

As the night wore on, Fred, Sam, Al and Rick all had me stand next to them for luck too. And at the end of the night I had made $85 in tips.

But I was horribly ashamed of how I had gotten it. I stood there passively while men touched me. It was awful!

After we cleaned the remains of the game up, Mama asked how much I had made. When I told her, she hugged me. "See how easy that was, Dennis? The rest will be easy too."

The rest?

Mama went into my room with me before bed and held a pretty pink nightie against me. Did she expect me to wear that? I was red with embarrassment!

"Try it on, Honey," Mama said in her "take no prisoners" voice.

Reluctantly, I did. It felt incredible! I adored it! It was cool and comfortable and the fabric rubbed my skin so sweetly. I looked in the mirror and couldn’t believe how good I looked.

Mama smiled. "So you like it?"

"No. And I can’t wear it," I said. "I’m a boy."

Mama looked at me as if I were a 10-watt bulb. "I believe you like it, Dennis," she said. Then she grabbed my fiercely erect cock and said, "You may not admit the truth, but your penis knows what it likes."

She was right.

I put the nightie on and got into bed. It felt wonderful against my nipples and it brushed very nicely against my distressed cock. What was happening to me? What should I do about my sore, throbbing cock?

As I was fretting, there was a knock on my door. Mama wouldn’t knock. I quickly covered myself with a sheet and began to tremble.

The door opened. It was Carl.

"Hi, Dennis," he said. "I just wanted to check and make sure you were all right. I know that was different and difficult for you tonight. Are you all right?"

"Yes," I said in a small voice. "Thank you." My cock was throbbing even harder. Carl was so good and kind to me. But I wanted him to leave. And stay.

"Good," he said.

Then he sat on the bed next to me. Oh, please make him go away, I prayed.

"Dennis, something’s been happening to you lately. Do you want to talk about it?"

I pulled the sheet even higher on me. What if he saw my nightie? Or my titties?

"Please, no," I said. "I don’t want to talk. I just want to sleep."

Carl honored my request. Sort of. He held my shoulder through the sheet and said, "OK, Buddy, but we need to talk sometime. Because being around you has really been affecting me these past few months too. I’m very confused by feelings I never had before."

What did he mean? No matter. He had to leave!

"OK, Sport," Carl said. Releasing my shoulder. "Just one last thing and you don’t have to answer. Did you like it when I rubbed your leg tonight?"

Oh. I began to shake and my eyes filled with tears. I could never answer that. I would just keep quiet and Carl would leave. And leave me alone.

He stood up, said good night, and began to walk to the door. What if he didn’t like me any more? What if he didn’t rub my thigh any more or call me "Sport" and "Buddy?" I did like him rubbing my thigh. I liked it a lot.

Carl opened my door and began to move through it.

"Yes!" I said. And changed my life forever.

Carl turned, looked at me and smiled. "Yes, you liked me rubbing your thigh?"

Oh, he was walking toward me. He sat down on the bed again.

"Yes," I said.

Carl kissed me, right on the lips. I don’t know who was more surprised, Carl or me. But it was a wonderful kiss, soft warm and gentle from a huge, rough, 40-year-old, heterosexual, oil-rig foreman. I felt warm and loved and sexually frantic. Just from a kiss. My first kiss.

He ended the kiss and looked at me with real admiration. "Pull the sheet down, Dennis."

I couldn’t! He would see my nightie and my titties and my stiff cock. But he was so masterful. I had to do it. I eased the sheet down to about three inches above my breasts.

Carl saw the nightie straps and smiled. "I knew I wasn’t turning gay. You’re a sissy, aren’t you?"

"I don’t know," I answered truthfully.

"You’re very pretty and very feminine. A man could be very happy loving you."

Did Carl just say he loved me? Not really. But I loved the praise.

"Pull the sheet down some more, Sweetheart," Carl said.

Reluctantly, I pulled the sheet to my waist. Carl could see my B-cup love pillows crowding my nightie.

Carl gasped. "How? I never….."

I guessed that he was impressed.

"You have a beautiful body, Sweetie. Let me see the rest."

"OK," I said, and pulled the sheet completely off.

Carl smiled as he looked at my silky legs and clear-polished toes. He saw how my tiny willie was tenting my nightie and said, "You need some relief very badly."

Gently, Carl reached under my nightie and touched my little cock with his huge, calloused right hand.

I shuddered with pleasure. Carl noticed.

Carl leaned over and kissed me as he milked my rampant little peeny. It was a lovely kiss and he fed me the tip of his sweet tongue.

Carl tickled my balls too. No one had ever done that and I was alive with erotic sensation. I could feel my balls begin to bubble as Carl licked my tongue and ran his thumb around the crown of my cock. I squealed and Carl picked up the pace. I was……..oh………cumming hard and deliciously. I was in heaven and all because I said, "Yes."

What a great word.

When I was through cumming all over my tummy, Carl’s hand, and my pretty nightie, Carl asked if I felt better. He was so considerate.

"Oh, yes, Carl. It was wonderful. Thank you so much!" And I kissed him again.

Then I did a very trampy thing. I asked, "Can I, you know, help you the same way you helped me?"

Carl beamed. Then he stood, pulled his pants and underpants down to his knees, and sat next to me on the bed once again.

I saw his stiff cock. It was a monster! Enormous! And red and angry-looking. His balls looked like baseballs and his bag looked as if it could hold a bowling ball. And his legs and balls were hairy. And manly. And wonderful.

I gasped and he chuckled softly.

I was ashamed to look at it at first. I hid my eyes and stole little peeks at its magnificence.

"Do you like it?" he asked.

I nodded shyly. "It’s beautiful."

"Have you ever touched anyone’s cock before, Dennis?"

"No, Carl," I replied honestly. Then I gathered my courage and touched it.

Carl’s cock was hot and throbbing. I loved touching it. There was a long, blue vein along the left side. I ran my soft hand along it and Carl gasped with lust.

I was making someone happy. I couldn’t remember the last time I was able to do that.

Carl’s foreskin was long and brown and wrinkled. I encircled it with my hand and eased it down over his pink cockhead. Carl groaned. He was leaking a lot of thin, sticky groo and some was running onto my hand. I thought I would like to taste it. That made my face hot with shame.

Carl leaned over and kissed me as I stroked his foreskin up and down with my warm, delicate hand. He kissed my shoulders and exposed my right titty. Would he kiss it? He would.

Carl licked my nipple and I felt an electric shock throughout my body. I arched my back, squealed and spurted my boyish cream in five thick globs. My nipples were apparently very sensitive.

Carl seemed delighted at my response. He took some of the cum from my tummy and applied it to his cockhead. I used it as a lubricant as I resumed my loving attention to his needs. Carl was too excited to last very long and I soon felt the joy of fulfilling a lover when he groaned manfully and almost drowned my hand in jet after jet of his copious spunk. Carl enjoyed what I did for him very much.

I was afraid of what he might want next, but Carl tucked me in, kissed me softly, thanked me for giving him the sweetest treat in the world, said goodnight, and left.

I began to cry. Something had been lost. Something had been gained. But my life would never be the same again.

 

 

Chapter Three – Adjustments

The next morning, Mama woke me at nine so we could go to 11 a.m. mass. She pulled the sheet back off me before I could think quickly enough and revealed the dried cum, both mine and Carl’s on my belly, nightie and sheets.

Mortified, I blushed. What would Mama think of me?

"Was it Carl or Bill? They were both incredibly hot for you, Sweetie. I’ll bet Carl. Did he kiss you?"

How did Mama know? I gulped and told her everything that happened.

Mama smiled. "And you liked it, didn’t you?"

I adored it, but I was so ashamed. I looked down and began to cry again. I was crying a lot, I know, but I couldn’t help it.

Mama hugged me. "There, there, Baby. It’s all right. I’ve known you were a sissy since you were about seven. It’s nothing to be ashamed of."

Mama knew? How did she know when I didn’t know? And what exactly is a sissy? I asked.

"A sissy, Dennis, is a boy or a man who really wants to be a girl or a woman. A sissy loves frilly, girlie clothes and his cock is hard almost the whole time he’s wearing them. A lot of sissies, though not all, want to make love to men. Kissing men. Sucking their big, hot, hard cocks. Even taking men’s big cocks into their tiny bottomholes."

Mama could see the fear in my face. I almost wanted to puke. Carl’s cock was enormous. I couldn’t…… He would rip me……..

Mama hugged me again. "Don’t be afraid. You’re not ready for that yet."

Yet?

"We’ll make gradual adjustments so that you’ll have a long, happy, wonderful, sissy life."

I sniffled, "But what if I don’t want to be a sissy, Mama?"

Mama looked at me. "I think you already are a sissy, Sweetie. But at 18, you can always be a man again. If you really want to."

That was almost four years off. What would I do? And what did Mama mean by adjustments?

The oil workers were off that Sunday and were all gone from the hotel when we returned from mass. It was Memorial Day weekend, which meant I had three days off from school, but I was always doing stuff at the hotel.

Mama really surprised me as we were eating lunch. "You never seem to have any time for kids your own age, Dennis." No kidding. I was always helping Mama "make ends meet."

Mama went on. "That’s why I invited one of your friends from school over for you to play and have a sleepover with."

I dropped my baloney on Wonder Bread sandwich. "Sleepover? Mama, I haven’t had a sleepover since I was nine and Dad left. You said I had to help you with the hotel all the time."

Mama smiled. "I was wrong, Dennis. Now I’m going to make it up to you."

I was very wary. "Who’s sleeping over, Mama?"

"Derek Carson."

RED ALERT!!!! I almost fainted. "Mama, Derek Carson is the biggest, toughest kid in our school. He’s six inches taller than me and outweighs me by 50 pounds. And I don’t think we’ve ever spoken."

Mama smiled again. "Do you remember when I came to school when you sang that solo in glee club last month?"

Was Mama changing the subject? "Yes. But so what?"

"I saw the way Derek Carson looked at you, Dennis. I think you’ll have a wonderful night. I’ve spoken to his mother. He's coming for dinner. Now don’t be rude to him."

"Rude? Mama, he’ll pulverize me."

"Oh, Sweetie. I don’t think so. Now let’s get you ready."

"Ready? Mama, he won’t be here for four hours."

"Just long enough," she said.

That afternoon, I was convinced that Mama was hell-bent on humiliating me and ruining what promised to be a brief life.

She took me to her room, sat me at her vanity and put MAKE-UP on my face. I cried and begged Mama to stop. I would be the laughing-stock of the school. Derek would kill me.

"Stop crying, Dennis. I can’t do your make-up. And pay attention. You have to learn to do this yourself."

Dead man walking. That was me. In school on Tuesday, I would be led to the schoolyard by the anti-faggot imperial guard, tied to a stake, offered a cigarette and a blindfold, and put out of my misery.

Mama disagreed. And when she finally dried my face and made me up, the results were startling. I was a doll. A beautiful, gorgeous, pulchritudinous, living doll. Big, blue, bedroom eyes. Full red lips. A perky nose.

The hair needed work, but even in my usual ponytail, I was a ten. And my woodie was back. Hard and insistent.

Mama noticed. "Stand up, Dennis and I’ll give you some relief. You’re in sore need."

I stood, ashamedly. Mama pulled my boy’s pants and underpants down and off and wanked me most deliciously into a frothy cum. I couldn’t look Mama in the eye, but I felt much more comfortable and my spirits rose a bit.

Mama was relentless. She removed the top parts of my clothing, exposing my boobies. Mama reached into a bag and pulled out what was to be my first bra. She had me put it on and hook it myself. My little puppies had been roaming free since their birth and they liked having a home. A strange, feminine feeling gripped me when I put on the bra. My little brother was erect again and Mama gave me another adventure in paradise.

Mama then produced a pair of silky, black stockings. Ohhhh. She showed me how to roll them into a doughnut, then slide them silkily up each leg. It was a wonderful feeling and <blush> I sissy-creamed yet again just putting them on. Mama smiled.

The garter belt was a big surprise. I didn’t know anyone used them anymore. But it certainly looked sexy in the mirror.

Mama gave me the prettiest, filmiest pair of pink panties and I eased them on to complete my lingerie ensemble. I sneaked little looks into the mirror. My goodness. I was a knockout.

Then Mama fiddled with my hair for a while. It needed a beautician, but it was long and full and silky.

The shoes were the worst. Mama bought me a pair of three-inch, stiletto pumps and it took me a long time to get to the point where I wouldn’t crash on every step. After about 90 minutes, I was mobile. The heels pushed my titties forward and my bottom back. And they made me take mincing little girlie steps. Exactly as intended.

Although I was terrified about Derek, when Mama had me put on a miniskirt and blouse, I began to think, for the first time, that he might not kill me. I was girlie enough for 95% of the hetero men in the world. Or so it seemed. I even began to feel a little like a girl.

We used every bit of the four hours to prepare, but the end product was a stunning me.

Mama sent me to my room so she could "prepare" Derek for me. He arrived at six on the dot and Mama must have told him many things, because she didn’t come for a trembling me until 6:32.

She was smiling and assured me that everything would be just fine.

It was a very different Derek than I was used to when I sissied into our living room. He was cleaned up, wearing a tie and jacket, and sporting the most adoring expression I had ever seen on a male. Was he crazy about ME?

Apparently he was. He stared in awe and reverence when I entered the room. Just for fun, I dropped a little hankie I was carrying and Derek dove to the floor to pick it up for me. First with Carl, now Derek, I had incredible power over men. I had never had power of any kind. Now I was like an emperor. Or an empress. Wow.

Derek held my chair for me, laughed whenever I said anything halfway funny and listened when I spoke during dinner. He filled my glass, helped Mama with the dishes and almost fainted when Mama suggested that we go to my room and play.

I couldn’t. What if he tried something? Mama wasn’t serious about us sleeping in the same room was she? I was already humiliated that Derek had seen me in girl’s clothes and make-up. Did Mama want him to, you know, do sex things with me?

Derek was handsome, attentive and very nice. Perhaps I had misjudged him. But sex things?

We got to my room and I closed the door. I didn’t want one of the hotel guests coming back early and seeing me. What if Carl saw me? He would probably be wildly in love with me dressed as I was. I shivered at the thought.

"Do you like Nintendo, Derek," I asked.

"Sure. I mean, if you do."

Derek was so willing and eager to please me. Perhaps if I were frank with him.

"I’m a boy, Derek. My Mama made me dress up as a girl. But I’m a boy. I have a cock, just like you. Maybe smaller. But a cock."

The sweet young man said, "You may be a boy, but you’re also the cutest, nicest, prettiest girl I’ve ever met."

He was a persistent one. Was he gay?

"So, you would want to do boy-girl stuff with me? Kissing and more? I mean, I could never do that with a boy, but would you really like to………."

Derek stepped forward and held me gently in his strong arms. I squirmed, but didn’t really resist. He kissed me sweetly and ran his hands up and down my back.

A boy my own age was kissing me. He knew I was a boy and he was kissing me. I didn’t think he was gay. And I knew I wasn’t. Why was I letting him? I didn’t want him to kiss me. It was wrong and I was so ashamed. But I didn’t want him to stop either.

Derek was a good kisser. No tongue, but very nice. He stopped and said. "That was great."

That kiss was more intimate than when I held Carl’s cock and made him cum.

I hated to admit it to myself, but I liked it very much. As I had done many times in the past 24 hours, I began to cry.

Derek held me and gently kissed my sobbing eyes. "What’s wrong, Sweetheart?" he asked.

"I’m a simpering little faggot. I’m a sissy. I’m so ashamed." <Sob>

Derek smiled and held my chin up.

"You’re a sweet, lovable girl. You’ve always been a girl. Your body was just slow catching up."

Derek was so sweet!

I didn’t resist when Derek unzipped my blouse in the back and removed it. Derek stared in wonder at my bra-held beauties. Then he reached back and clumsily unhooked my brassiere. The two little puppies with big, brown noses, Sparky and Scooter, were free again.

I surprised myself by saying, "You can kiss them if you want, Derek."

Derek’s eyes filled with moist joy. He asked me to lie on my bed, then removed all but his undershirt and underpants, which, for the record, were clean. Meanwhile, I wiggled out of my skirt and kicked off my heels. Derek gasped when he saw my garter belt and pink panties. Then he lay next to me on the bed.

Derek looked at me as if he were seven and I was the red truck under the Christmas tree. He kissed me again, rubbing his body against me. I was very steamed up. Hot and excited. I pushed his undershirt over his head and off. Derek’s torso was very nice. Not hairy and manly like Carl’s. But very nice for a fellow 14-year-old. Derek began to kiss and lick my titties.

"Derek," I said. "Wait! They’re so….. Oh, Derek. Use your tongue right there. Oh, that’s wonderful. Mmmmm. They’re very sensitive. Gently. Ohhhhh."

Derek was gentle and enthusiastic. If he kept that up, I would cum. He kept it up.

"Derek!!! I’m cumming," I squealed. Then I climaxed hard into my new, pretty, pink panties. Mama would understand.

Derek was merciless. He kept worshiping my soft pillows. Then the bad/good boy reached into my gooey panties. I was so embarrassed. All that cum. But Derek rubbed my own goo all over my stiffening prickie and then <gasp> rubbed cum all over my sensitive bag of baby balls.

Derek kept kissing my nipples as he cum-massaged my balls, then prickhead. I was squealing like the world’s biggest sissy when I came for the second time in ten minutes. I predicted a very cummy evening.

I decided that Derek must be in some distress. How could I relieve that while showing proper appreciation? I didn’t really want to suck his cock, because then I would be a cocksucker.

But Derek had been so nice. And everything had been fun so far.

I kissed him as I peeled his underpants. Derek had a whopper of a cock for a boy his age, thick and juicy, even though it was much smaller than Carl’s. The skin was back and the peehole was drooling like a kid in a candy store. I ran my soft hand up and down its length. Derek groaned and kissed me sweetly.

It surprised us both when I got on my knees and kissed his cockhead. Derek groaned again and I tasted my first pre-goo. It was good!

In for a penny, in for a pound. I looked at Derek. He was hoping I would take his cock in my mouth and suck him until he fainted. I gave the head a little lick and giggled. He arched his back. It was great to be finally in charge of something. Derek touched my head gently and looked at me imploringly. The lad was in extreme need. And I was his antidote.

I swirled my tongue around the head, very slowwwwwlllyyyy. Derek said "Aaaaaahhhhhhh" or something similar.

I still wasn’t technically a cocksucker. But suddenly I wanted to be. I sucked Derek’s cockhead into my little mouth. It was hard, but satiny smooth and it tasted salty but nice. I peeked at Derek. His eyes were closed and his face was a mask of ecstasy. I sucked up and down and swirled my tongue around the head. He was really leaking badly and it seemed as if something gooey would happen soon,

What would I do? I couldn’t swallow his cum. That would be so embarrassing. Even if Derek didn’t tell anyone, he would know I did it. And so would I.

But he was sort of vibrating. And thrusting his cock at me. What if….. Oh, no! Derek was cumming. And I had my mouth all over his cock.

Suddenly my mouth was filled with cum. I couldn’t breathe! What could I do?

I swallowed. Big sticky blasts of cum.

It was so ashamed. Now I was a cocksucker and a cum-swallower. And I couldn’t really blame Mama. Derek didn’t exactly hold a gun to my head.

Oh, yeah. Derek. He was looking at me like no one ever had before. Was he disgusted at me for being a cocksucking, cum-swallowing faggot?

It didn’t appear so when he gently pulled me up to him and kissed me for a half hour.

When we stopped, Derek said, "This has been the happiest day of my life."

Then he kissed me again. And pulled my panties down and began to tickle my very aroused cock.

What he did next really surprised me.

He got on his knees and began to do for me what I did for him. He kissed my cum-soaked pricklet all over. He licked the head, then sucked it. Oh, Baby. That was good. I was hard as Depression times when he began to lick my balls. That was the icebreaker. I just said the heck with my hang-ups, screamed his name and climaxed a gallon of sissy cream into his face.

I was terrified! Poor Derek must have been humiliated. His face was covered with more cum than I knew I had in my body. Would he hit me? Storm out and leave, telling everyone in school what a faggot I was?

Not exactly. Derek began to laugh. Then he said, "Wow. You really liked that. You can’t fake what you just did."

He was right. Including the fact that I liked it. He was so sweet.

Derek excused himself for a minute to wash his face. Then he got back in bed with me and held me in his arms. "You’re the best girl in the world, Denise," he said.

Denise? OK. I could live with that. Even though I wasn’t a girl, I loved the compliment.

I was a pretty good girl.

Derek had brought something back from the bathroom and he dipped his fingers in it. Then he kissed me some more. I think I liked the kissing most of all. Then he kicked things up a notch. Derek’s fingers were slick with some lubricant. As he kissed me, he tickled my tight little anus ring. His other hand cupped my bubble bottom.

I gasped at the sensation. Was he going to put his finger into my bottom? He was. For the first time, something entered my bottom. Derek’s finger felt divine, especially with all the accompanying kissing. Then he slipped a second finger in. Oh, my poor prickie! It was red and sore and no one was even touching it!

Then he found my prostate!

Had Mama prepped him for all this during their little conference? No matter. When Derek rubbed my prostate, I would have followed him to the Bermuda Triangle during a hurricane. I squealed with intense, gut-wrenching pleasure and spurted blast after blast of sticky cream. I was sobbing with lust and finally begged him to stop. When my heart rate slowed, I looked at Derek. He had the silliest, happiest grin. He really loved pleasing me. Had I already fallen in love with him?

I’ve discovered since that sissies fall in love very easily. With multiple partners. And men love their sissies.

I nursed on Derek’s cock, bringing him to two bone-breaking cums. I swallowed it all. Yum. Then I got up, made tinkles, took my stockings off, brushed my hair, put my nightie on and got back in bed for sleep.

Derek watched it all, as if it were the greatest show on earth. Defying nature and gravity, his cock was stiff once again.

I was tired, but curious. He kissed me, then spooned up behind me. He reached under my nightie and entered me with two lubed fingers yet again. More prostate torture? I didn’t know if I could…… That wasn’t a finger! The rascal had pulled out his fingers and slipped in his cock.

He was fucking me!

I was being fucked!

It was fantastic!

Oh, I felt so girlish. I was in bed in my pretty nightie and a boy had his big cock in me! And he was running his lubed thumb all over my pink little helmet. He kept thrusting in and out. He was clipping my prostate and it was so hot!!!! My balls were bubbling. He was kissing my neck telling me he loved me. That did it. I yelped and came hard. Then squealed and spurted again. Derek picked up the pace, quivered, and let a big, hot, gooey load go into my squishy bottom.

Now in addition to being a cocksucking faggot, I was a buttfucked faggot.

It was dreamy!

 

 

Chapter Four – Impressing Mama

That bad boy Derek fucked me during the night, then twice more in the morning. I had to poop really bad after the first time, but the next ones were pure pleasure.

As I kissed Derek goodbye, with promises of renewed meetings, I thought about Mama. Why had she set the night of love with Derek up?

I could think of two reasons and they were probably both true.

First, Mama probably thought that when I was unable or unwilling to dress as a boy anymore, I would need protection around school. Having Derek as a love slave guaranteed that no one would touch me.

Second, and this was the one I really didn’t like, Mama wanted to make sure that I could take on those big oil men who would keep us out of the poorhouse. If I could take Derek’s boyish equipment in my mouth and bottom, I would have less of a problem taking that tree log of Carl and his fellows.

Was I just a hotel asset to Mama?

No. I think that she thought she was really doing the right thing for me. And helping us financially in the process was a bonus. If I didn’t believe that, I would have been really mad at Mama. So I believed.

I especially believed that I didn’t want to talk to Mama the nanosecond after Derek left. I wanted to take a bath and get all that cum off and out of me. And think about what had happened.

But, of course, Mama appeared magically.

"Did you have fun with your new friend, Dennis? Or did he call you Denise?"

I didn’t need teasing at a time like that. "Please Mama. Don’t tease me. This is tough for me."

Mama softened. She hugged me. "OK, Sweetie. You’re right. How was it?"

I looked down. "Horrible!" I said loudly. "And wonderful," I added softly.

Mama smiled. "You’ve described life. Woody Allen says life is divided into the horrible and the miserable. Horrible and wonderful sounds a lot better."

Mama persisted. "Did you kiss him?"

"Mama, I think you were watching when I kissed him goodbye. No games, Mama. Please."

"OK, Honey. Then did you make each other cum?"

I couldn’t look at her, but I told her the truth. "<Sob> Yes."

"Was it nice?"

"<Sniffle> Very nice."

Mama beamed. "See? I was doing what was best for you. You would never be happy being a boy."

"But Mama, I am a boy."

"Not if I can help it. Did you suck his cock?"

Too much detail, but I answered. "Yes. And he sucked mine."

That startled Mama. "That’s great! Did you enjoy it? All of it."

"I guess so."

"What didn’t you like? Was he mean to you? I’ll……"

"No, Mama. Derek was very good to me. It hurt a little when he put his thing <gasp> in me. But then it was great."

"He fucked you? Oh my little girl. Good for you. Welcome to womanhood. How did you like it?"

"Like I said, it hurt a little the first time, but…."

"The first time? How many times did you two do it?"

"Four. Is that OK?"

Mama looked stunned. And happy. I had actually impressed my mother. A first.

"I’ve underestimated you, Denise. Is it OK if I call you that? I’m proud of you."

It was a strange thing to impress my mother with, but it was a start.

 

 

Chapter Five – Denise Goes to School

Carl and the oil men had an on-site emergency and never got home until mid-day on Tuesday.

Tuesday morning, I had to go to school knowing that one of my same-sex classmates and I had been totally intimate and that he could say all kinds of true things about me that would doom me with my peers forever.

That was the small concern.

The big concern was that Mama dressed me for school in a skirt, heels and blouse. A blouse that revealed that I had a bra supporting a very nice rack.

I was almost crying too much for her to put on my make-up. I begged and pleaded, but we were working on Mama-logic.

It was way too hot to keep wearing loose sweats. Someone would notice that I had titties and would say things we could not foresee.

School was almost over for the year and it was better to get my girlishness out of hiding now so that it could be dealt with over the summer and muted by the time I started high school in August.

I was a very pretty girl and would be adored, not reviled.

Derek would protect me.

Point one was probably true, as was, I hoped, point four. Point two was a pay-me-now-or-pay-me-later deal. But what if I wanted to stop taking "allergy shots" and start high school as a boy? Mama snickered when I said that. Point three was true. I was cute and hot. But wouldn’t I still be the object of derision by people for whom "acceptance" only means getting into college?

Mama drove me to school and explained to the principal that I would now be attending school as Denise and dressing as a girl. My life flashed before me. The die was cast. No turning back. Word was out.

Was the principal leering at me? Your principal is your pal. Maybe point three was true.

I entered my first period classroom and the principal whispered to Mr. Evans, my math teacher. Mr. Evans smiled at me. The other kids just stared. I was the prettiest girl in the class by the number of lengths Secretariat used to win by.

The boys noticed. So did the girls. No one was more surprised than I was, but the kids left me alone. Switching classes, they all asked what happened.

"It’s my mother’s idea," I said. Vague truth is a good thing.

Bobby Flynn said, "You’re beautiful, Dennis." He didn’t care about being called gay or anything. I saw Derek in the hall and smiled. He smiled back, but kept a wary eye against harassment. He was protecting me, just as Mama said.

Could Mama have been right about everything?

 

 

Chapter Six – Denise Comes Home From School

It wasn’t all roses the first day. I heard a few calls of "faggot!" from both boys and girls and someone even knocked my books out of my hands. But all in all, I was much more accepted than I ever dreamed that I would be.

I wasn’t happy about everything when I got home from school. But I wasn’t unhappy either. Could I really "pretend" to be a girl and get away with it? And like it?

Mama asked me all about school and seemed very pleased with the results. She told me I looked tired and suggested that I lie down for a while. That was a first. But Mama knew that the tension of the day had worn me out. I went into my room and removed my school clothes, stripping to my bra, panties, stockings and garter belt. It felt so good to get out of those stiletto pumps Mama insisted I wear. They sure made me look good, though.

Since Derek had left me the previous morning, I had been experiencing sort of a general malaise. I didn’t know what it was, but I sort of ached all over.

I lay on top of my bed and closed my eyes.

I began to think about things. About men, really. About Carl. And Derek. And even Bobby Flynn, who had said I was pretty that day. My cock was pushing my panties.

I sort of patted my titties through my bra. Maybe it would be more comfy to take the bra off. I did so and my growing, fleshy pillows flopped free.

I still had that ache. Like I needed to do something. I thought about what Carl would think if he saw me now. Lying on my back in my bed. Wearing only stockings and a garter belt. My nice titties bare. Their nipples erect. I pinched them just a little. Oh, that felt good. But it made that ache worse. My pricklet was stiff and my panties were full. Maybe if I just rubbed myself down there, that ache would go away.

I pulled my cock out and saw how wet the tip was. I rubbed the gooey stuff around the head with two fingers and once again thought of Carl. He was so big and rough. And his cock was huge. If he came in my room right then, he could have done anything he wanted to me. Disgusting things. Well, maybe not totally disgusting, but I was a boy and shouldn’t have a big hairy man on top of me. Warm and rough. Rubbing his big body against my little self. I would be just a helpless little girl. I meant boy. He would probably take his cock out and order me to suck it. I couldn’t resist, because he was so big and strong. Carl’s cock would be all red and angry and the peehole would be leaking and I would……. Ohhhhh. I began to ejaculate my sissy cream. My stomach was wrenched. It was gushing out! My tummy was covered with it. Carl!!!!!!

I didn’t really understand why that happened, but thank goodness the ache was gone. I was pretty sure it would be back. Now that I had started spurting my sticky cream, it appeared that I needed to keep doing it fairly regularly.

That was OK with me.

I dozed off and Mama woke me at six to call me to dinner. I’m sure she noticed the big splotches of dried cum all down the front of me, but she kindly left it alone. She put out an outfit for me – a miniskirt and tight top and black, silky stockings. Were we going to a club or something? Then I remembered that the oilmen had returned and would be checking me out.

I was scared. They would want to do disgusting things. Especially that Carl. I hoped.

At dinner, Mom told me that we got three new guests that day. Two of the three had moved from what Mama called "the Harpers’ fleabag across the street." It appeared that I was a bigger attraction than that tramp Mary Ellen Harper.

Pussy is no competition for a sissy’s charms!!

I helped Mama clean up and went to do my homework. At nine, I left my room to do some hotel duties and ran into some of the men who had napped and were now stretching their legs.

They had never seen me fully dressed as a girl and their eyes were bugging out. They kept telling me how pretty I looked and asking me to stop by their rooms for a chat.

Carl was the last to awaken. When he did, I knew what my night would be like.

He saw me and his heart melted. The look I saw in his eyes was one I had only seen from Mama, Daddy before he started drinking, and Derek.

The man was in love.

Who was I to fight that?

I was such a little tart. I got into a pink babydoll nightie, pulled on pink stockings and pink mules, let my hair down and brushed it, washed my face, brushed my teeth, put on a robe and knocked on Carl’s door.

"Come in," he said.

When he saw me, he said. "I was praying it was you, Denise."

Everyone was calling me that.

"I just wanted to see if you were all right," I said. "You’ve been working so hard."

Carl smiled, "Thank you, Sweetheart. Come sit with me. I understand you’ve had some interesting times too."

Mama was such a big mouth. "It’s been horrible and wonderful," I said as I sat next to him on his bed.

Carl said, "If you take that robe off, we can add to the wonderful."

I should have said, "Thank you, Carl, but I’m a boy and I’m only dressing like this because my mother is making me. Good night!"

Of course, that was not what I wanted by that point. I said nothing; merely removed my robe and showed Carl my luscious femininity.

Carl gasped in awe. He was a man of taste, obviously, because I had it all. Pretty face, girlish body, cock and balls.

He arose, then stripped off all his clothes. That was a bit forward, but it was pretty obvious that I wasn’t there to bring him milk and cookies.

Carl’s body was well-used. It was scarred and muscular. And very hairy. Had his cock grown since I saw it three days earlier? It was boring a hole into his belly button.

Oh.

Carl sat in a straight chair and beckoned me. I straddled his right leg and sat on his naked thigh. I opened so widely that the hairs on his leg tickled my anus as he kissed me. I could feel his leg hairs scraping against my sensitive pink bag as well. Oooooohhhh.

Carl told me what a pretty girl I was. And kissed me again.

It was so exciting. I twirled his chest hairs in my tiny fingers as he kissed me. Then he reached under my nightie and held my pricklet with his raspy, but gentle fingers. He skinned me up and down as his hot breath covered my neck and his free hand caressed my bottom.

I was so needy for him. I wanted it all that night. Of course I came, squealing his name and shuddering through a ball-busting climax. That was just the appetizer. Carl looked me in the eyes and I knew what my destiny told me to do.

I slipped to my knees and held the biggest, wettest cock in the world in my delicate hands. Carl groaned as I handled him lovingly. He grunted when I planted soft kisses along the length of his rammer, making little smoochie marks with my lipstick.

Carl was clearly in love. Or at least in considerable lust. I said, "Carl. I think it’s too big to get into my mouth, but I’ll try. I’ll lick it the best I can anyway."

Opinion differs on whether a cock should be swallowed or merely licked to bone-shattering climax.

I tried both methods and they sure worked. I licked his cock from the underside of his balls to his peehole. Then back down again. I sucked each ball, which made Carl lurch. I tickled the underside of his mushroom with my tongue, which made Carl moan loudly. Then I stretched my little mouth and got most of the head in. I sucked and licked like a girl serving her man.

Carl and I kept eye contact, which was very sexy and intimate. It also gave me an early warning when he winced in the first orgasmic pang, then exploded into my mouth.

It was a hot torrent of cum, drooling from my mouth and sliding down both sides of my chin, like lava from a volcano. And almost as hot.

Carl groaned with joy. He grunted that it was the best orgasm he had ever had.

I was so proud.

But I was worried about what might happen next. What if he tried to FUCK me?

I could never. It would never. It was against the laws of geometry. And physics.

Carl apparently was a law-breaker.

He picked me up and carried me to his bed, kissing me sweetly the whole way.

He laid me on my back, then lay next to me on his back.

When he explained to me what he wanted, I blushed in shame.

"I want to eat your asshole, Sweetheart, make you cum, and loosen you up for me to fuck your pretty bottom."

Adrenalin surged through my body. I was prepared for fight or flight. I chose neither.

I straddled Carl’s shoulders, on my knees facing his feet and lowered my intimate hole over his mouth.

Carl ate me out thoroughly and thrillingly. He started slowly at first, with hesitant little licks of the soft flesh between my bottom cheeks. Then he took gentle, tiny licks of my rosebud. The first time one molecule of Carl’s tongue touched my hole, I shot my sticky cream all over Carl’s chest, screaming as if I had been shot. I almost fainted. Carl’s chest hairs were matted with my hot goo.

Carl began to devour my hole in earnest. Licking, slurping, grunting as he dug into my secret places. As an oilman, he knew how to dig and drill. He had a long, stiff tongue and it was the singularly most exciting and scary moment of my life.

I shuddered and helplessly ejaculated once again. Oh, Glory, it was powerful! Gobs of sissy cream leaping through the air, punctuated by girlish squeals. Carl could keep doing that as long as he liked.

He held my hips in his rough, but gentle hands and ate his carnal meal for another fifteen minutes and yet another of my cums, though that time I was only half hard and dribbled cum rather than spurted it. It still felt like being hit by a 50-foot tidal wave.

Boys couldn’t possibly have that much fun, could they?

When Carl pronounced me ready for my fucking, I began to cry. Carl’s heart melted and he kissed away my fears, then put me on my back.

"Girls should be fucked on their backs, Denise. It shows them who’s in charge."

I loved a man to be in charge. Or at least think he was in charge.

Carl covered me with his huge body and put my pink-stockinged thighs on his shoulders. He looked at my pretty eyes and kissed me. Then he looked at my soaked, relaxed hole and smiled.

My doodle was limp with fear and overwork. I trembled, but wanted Carl’s cock in me very badly. I sneaked a peek at its magnificence one last time before it murdered me. It was a monster. It would tear me apart.

I whimpered. Carl shushed me softly, then touched my ring with the sopping tip of his big boy. There was fear and lust on my eyes as Carl pushed.

It hurt!!! Horrible pain!!!!

But only for a second. Then my bottom hole welcomed the invader and with one steady thrust, he was all in.

I almost expected another jolt of pain. But it didn’t come.

I felt full, but warm and loved. I reached down to feel the connection, just to be sure that Carl was all in. He was – to the hairs.

How had I ever done that? Carl had prepared me beautifully. He was a wonderful lover.

Carl began to move. Oh. I felt his horse dick scrape my prostate. The English language needs a new word to describe what a pleasure that was.

Carl kissed me and fucked me. We were both in an erotic trance. I wrapped my pretty legs around him and pulled him toward me, making him fuck me harder. I was whining and whimpering and begging for more! Carl gave me long, hard strokes and grunted out his love.

My peeny, soft as yogurt, flopped with each thrust. Then I felt another orgasm approaching. But my cock was so soft. No matter. It built in intensity, doubling with each of Carl’s now frantic thrusts. Carl was close too. My cock just lay there, but my balls were telling me ……….Oh………….I slammed into a wall at 100 mph, fell off a cliff, was hit by a left hook. I shuddered in a gut-clenching orgasm just as Carl gave me a bucket-size cum enema. And I drooled out three watery drops of my own cum.

Being a girl didn’t seem to be all that bad.

 

 

Chapter Seven – Winners

The next two weeks went by in a blur. A cummy blur.

I guess the strangest part of my life from then on was the way my mother began to treat me. Until I became Denise, Mama loved me, but she seemed kind of annoyed to be burdened with me too. She liked men, but she used men too. I got the impression, probably justified, that she was using me as well. I was her servant around the hotel, although she really did need my help for us both to survive economically.

Then she got the bright idea to turn me into a little sissy sexpot, attracting men to the hotel. That succeeded way beyond Mama’s wildest dreams. In the three weeks I had been Denise, our occupancy tripled.

I was every big, burly oilman’s fuck dream. I certainly wasn’t going to make all their dreams come true, but they liked being around me. Who really wants all their dreams to come true anyway? I mean, then what?

Mama was probably pretty cruel to turn me into a girl against my will. But I’m guessing that if I had really resisted, she would have backed off. At least I hope so.

Anyway, she treated me with a lot more respect for then on. As a fellow woman, almost. And her greatest economic asset, not an economic burden.

And she did love me. I’m pretty sure.

She did get people to help out with all the housekeeping chores, now that we were so full and busy. She hired the Harpers, who had to close their hotel across the street. It was Mama’s finest moment when she offered Linda and Mary Ellen Harper rooms and board and a small salary to help run a successful hotel – the Acme.

So now the men who stayed at our place had four chances for sex almost every night, though I was clearly the preferred prize. I think a lot of them were thinking of me when they blew their cum into Miss Mary Ellen Harper and her trampy mother.

As the school year wound down and the Harpers were doing all the Cinderella work, I got to be the fairy princess. Most days after school, I would wear a tiny bikini Mama bought for me and sun myself in the hotel’s small backyard.

Sometimes one of the guests would come out and put some lotion on me. Mostly they would just peep out their windows and punish Elvis.

Carl and Derek were my favorites, but Carl betrayed me! His company moved him to a job on the west coast! I only got to feel his hot cock in my bottom 23 times after that first night. I was heartbroken when he left.

Oh well. There were lots of other nice men in the hotel. And sissies are obligated to share themselves with multiple admirers. It’s in the Sissy Code.

At school, Derek made sure that no one could get close enough to me to harass me or romance me. Except for Bobby Flynn, who seemed openly smitten with me, but Derek seemed to be fine with that.

Hmmmmm. I wondered about that.

With our new prosperity, Mama bought me all kinds of pretty things. I really did feel like a princess and men from ten area codes noticed.

I wore the cutest little black dress to junior high graduation. At the party after, I was joined by Derek and Bobby.

Derek and I had enjoyed four sweet, extended liaisons, not counting the times we found a dark corner at school and played slap and tickle.

He seemed so comfortable with Bobby mooning over me. I couldn’t figure it out.

Bobby even asked, in front of Eric, if he could stop by my place some time. I was so mad at Derek for not being jealous that I said, "How about this afternoon, Bobby?"

Bobby was ecstatic and Derek was indifferent. Huh? Was Derek tired of me already? Was I that dull and sexless? I would show Bobby I wasn’t, just to spite Mr. Derek.

Bobby asked his mother for permission, then came home with Mama and me.

The hotel guests were all at work when we got home and for some reason, Bobby seemed disappointed.

"I thought you had a hotel full of oil workers, Denise," Bobby said.

I looked at him oddly and said. "We do, Bobby. They’re all at work."

That satisfied him. A strange boy.

Mama suggested that I take Bobby and show him my room. A fine idea. He was very cute and he liked me. And was nice to me. That deserved a reward.

Bobby seemed very excited when we entered my room. Men, I discovered, always were. Some almost hyperventilated.

Bobby was different about it. He oohed and aahed about my feminine touches and then he said the strangest thing. "You’re very lucky, Denise."

Then things got stranger. Bobby began to cry.

I was dense but not impermeable. Bobby was a sissy, just like me. Except he apparently had figured it all out on his own.

That was why he was always telling me I was pretty. He wanted to wear my panties, not pull them off me.

That was why Derek wasn’t jealous. He knew. How did he know?

I held Bobby and comforted him.

I was living his dream, he said.

But I think I made things even worse by hugging him. He felt my breasts against him and said, "YOU HAVE REAL BREASTS TOO?" And he began to sob harder.

Poor Bobby. I was duped into this and I had the killer bod, the wardrobe and the hotel full of rough, hard men. He probably scrambled for crumbs all his life and I had the whole bakery.

I didn’t know how to make him feel better so I kissed him. That slowed his sobs a little. Then I asked, "Who knows about you?"

<Sniff> "My Mom knows, but she won’t admit it to herself. My Dad ran off. He doesn’t care."

I knew the feeling. "Anyone else?"

"Some boys suspect. Derek knows."

Aha!!!! I thought so. I already had the answer figured out, but I asked. "And how does Derek know?"

Bobby blushed. He stammered, "Well, Derek and I……"

How long had this been going on? I asked.

"About a year," Bobby said. "But he dumped me when he met you."

Another competition I had won. I was on a roll. But dumping Bobby was mean.

"There are other boys in the world, Bobby."

"I know. But I’m scared. I don’t know which ones will fall in love with me and which will run. "

"I could help you there. Maybe you would like to meet some of the nice guests here."

Bobby almost drooled.

I felt sorry for him and decided to help as much as I could. "Would you like to try on some of my things?"

Bobby trembled with excitement. "Oh, please!"

Bobby knew how to put on make-up. Although my shades weren’t perfect, they were close enough for him. He tried on a white babydoll and my cock was appreciative of his beauty.

"You’re very cute, Bobby. Would you like to try on a pair of white stockings and a garter belt?"

Bobby was very agreeable to anything femmy.

As he was putting his stockings on, I stripped to my hose, garters and heels. My little soldier (a WAC, actually) was at attention. Bobby was a cutie. When Bobby tore himself away from the mirror, he finally noticed that a rampant, pretty, half-naked, teen she-male with very nice titties was in the same room licking her lips and beckoning.

Bobby accepted the invitation.

He sissied over to me in his high-heeled mules. I gave him a sweet kiss and felt his Johnson. It was very excited. Was it from me or the girlie clothes? No matter. I got on my knees and licked him to a screaming cum. Then he got on his knees and showed me why he had been Derek’s boyfriend for a year. That sissy could suck a cock! I was breathless when I spurted all my sticky juice into his sweet mouth.

We cuddled and kissed on the bed for a while and I asked him about Derek and him.

Blushing, he told me that Derek and he had been at a scout campout about a year earlier when Bobby slipped into the woods to answer a call of nature. Pulling his scout shorts back up he saw Derek nearby. Had Derek seen his pink panties? No. He would have said something.

Bobby forgot about it for a week or so until one day he was at the Mall waiting for his Mom to try on something or other.

Derek saw Bobby and said hi. Derek had never spoken to Bobby all that much, but he asked if Bobby wanted to get a Coke or something while Bobby’s Mom obsessed over blue vs. red.

Bobby was flattered that Derek was being nice to him. He didn’t know how nice Derek planned to be. Derek walked Bobby over to the food court and bought them each a Coke.

Then Derek made his move. "I saw your panties, Bobby. Are you a sissy?"

Bobby’s answer was clear. He began to cry.

Derek held Bobby’s hand under the table and said, "It’s OK, Bobby. It’s OK if you’re a sissy. I like sissies." Then, under the table, Derek unzipped Bobby’s pants, reached in. and stroked his little sissy cock to a creamy cum. Bobby was in love!

Bobby and Derek’s love affair flamed white hot, with long, cummy afternoon sessions in Bobby’s house when his Mom was at work. Bobby was surprised that Derek was such a good cocksucker himself. Was Derek a sissy too?

Bobby adored Derek, but the affair ran its course, with both eager for new partners. Bobby wanted men. Derek wanted a new sissy. Derek got his wish a month earlier. It appeared Bobby would get his that day.

I asked the little cutie, "Would you like a big strong man to hold you and kiss you, then eat your little bottom and fuck you with his big cock?

Bobby was so excited that he spurted his cream on me. He was so expressive.

Then I worked my magic. The men were home from work. I picked up the house phone in my room. "Bill? Hi. It’s Denise."

Bill reacted as if he had won the lottery. "Hi, Denise. How are you?"

"Fine, Bill, thank you. Say, Bill, I just graduated today and one of my girlfriends is visiting. She’s very sweet and pretty and likes men. Would you like to meet her? And could you bring a nice friend for me?"

Oh, yes.

Nanoseconds later, Bill Kerns and Jay York were knocking on my door. Bobby was in his nightie and stockings. I was in bra, panties, hose and heels.

After a few obligatory moments of small talk, Bill escorted the delighted Bobby to his room. I gave Jay the evening of his life.

Bobby had to go home by ten, so he sissied into my room at 9:30, full of love and sweetness and a tummy and bottom full of cum. Bobby covered me with kisses, thanking me for my hospitality and affection.

He sadly pulled on his boy clothes, but I made him smile when I said he could come by any time.

Bobby gave me a big tonguey kiss and volunteered to help out with the hotel guests any time.

Was it was any wonder that we soon became the biggest hotel in town?

We understood competition.

 

 

 

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© 2002 by Gingerfred Man. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, compilation design) may printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without express written consent of the copyright holder.