How I Became a Cheerleader Ch. 13

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
DMaster_14
DMaster_14
1,066 Followers

There was still enough drama to embarrass me before graduation. Trent and I had held out as long as we could but by the third weekend after the cruise before it happened. That night we had gone to his house, Jason and Heather were at some charity ball and after more than two hours of sex Trent and I had fallen asleep in his bed.

We had started with a pizza for dinner and ate while we watched a movie in the media room and then started to get intimate. I had sat on his lap and we had made out for most of the film. I felt him harden beneath me and wiggled on his rod. Finally I was ready for him, but wanted to have a little fun.

I climbed off him and ran out of the room with him right behind me. I led him into the pool room and let him catch me right at the edge of the pool, but I still had enough momentum to pull him into the pool with me. He came up sputtering and glared at me.

"Now that wasn't very bright." He accused. "What are you going to do about clothes to go home in?"

I swam to the shallow end and stood long enough to strip and tossed my clothes onto the deck. Standing naked in the pool I looked innocently at him and said. "It is your fault for chasing me in here. I guess we will have to dry the clothes before I go home. In the mean time, since we are in here, we might as well enjoy a nice swim."

I dove cleanly back into the water and surfaced on my back. My tits pushing up the water and my clit standing as hard as was possible, considering the hormones I was on. Trent wasted no time and shucked he clothes off and chased me around the pool.

I shrieked in mock terror and tried to escape him, but not very hard. He caught me at the steps in the shallow end and pushed me down onto my hands and knees. I felt him pull my cheeks apart and felt him slid the large head of his cock against my rosebud.

"You have teased me long enough, now you are going to get what is coming to you." He snarled.

"Good, fuck me hard you bastard." I screamed and then his dick plunged into my pussy.

"OOOHHHHH GGGGGOOOOODDDDDDDD. " I hollowed. "I have missed that."

"Well you aren't going to miss it tonight." He grunted as he drove all the way into me. "By the time I am done with you, you won't be able to walk for a week."

"God I hope so." I said, pushing back against him, joining his rhythm as he fucked me. The slap of our bodies echoed in the pool room, the water splashed as he pounded into me and I drove back against him. His hands reached around and grabbed my nipples, pulling them sharply.

I groaned in delight and reached back with one hand and rubbed my clit with my wrist as my fingers played with his swaying balls. Trent shuddered at each touch of my hand and he pulled harder on my tits. I could feel my pre-cum dripping on my arm and his lubing my channel as he worked into me.

We were both panting in a matter of seconds. The sexual tension had been building all week and this was our first chance at releasing it. Neither of us was going to last long, but that was okay, we had hours yet.

"I am gonna cum baby." Trent cried.

"Do it, fire it into me." I screamed back. "I need it to put the fire out. Cum for me now." I squeezed his balls and felt him shudder and drive as deep as possible into me. His cock flexed and began spitting ropes of cream deep into me. That triggered my own orgasm and I screamed in delight as I came at the same time.

My load dribbled out of my clit into the pool and Trent held me close as he emptied his balls into me. He lay on top of me and panted for breath as he finished cumming in me and then stood and fell backwards into the pool. I slid bonelessly down the stairs and submerged myself in the clear warm water with him.

I broke the surface and Trent was right beside me, still trying to catch his breath and I snuggled into his arms.

"I missed that." I told him gently.

"Me too, I love you Janie" and he kissed me tenderly before he picked me up and carried me to his bedroom for a repeat performance.

The morning light awoke me and I snuggled deeper into his arms before I opened my eyes and saw his bedroom. I sat up with a start and Trent grunted in his sleep.

"Wake up lazy. It's morning." I told him sharply.

Trent sat up just as quickly. "It can't be."

"Well it is." I told him pointing at the clock and it read eight fifteen.

"We are so busted." He said looking at me.

"Tell me about it. I am going to be grounded for life. Where are my clothes, maybe I can sneak out of here without seeing your parents."

"Not gonna happen." He said morosely. "We left them down at the pool last night. And Mom and Dad always have a swim before seven each day."

"Oh shit." I said softly.

"It is not like they don't know we have been sleeping together. They bought the cruise tickets remember?"

"Yes, but is different than doing it under their own roof." I said.

"Yeah, you have a point." He agreed. "In that case, we might as well just face the music."

"But what am I gonna wear?" I demanded.

Trent sat in thought for a minute and then got out of bed and tossed me one of his dress shirts. It was far too big for me but it covered me. He helped me roll up the sleeves so I could at least see my hands but that was all we could do.

We opened the bedroom door and hanging there was small bag. I peeked in and there were a fresh pair of panties. I showed Trent and we both winced, so much for hiding from Heather and Jason. I slipped them on and we headed downstairs.

Jason and Heather were seated at the kitchen table drinking coffee, the remains of breakfast before each of them. They looked up and smiled brightly as we came into the kitchen.

"Good morning you two," Jason said cheerfully and he pointed to the other side of the table. "Breakfast?"

"Yes please." Trent said looking down at the table.

"Did you sleep well sweetie?" Heather asked me politely.

"Yes thank you." I said softly.

"Is something wrong?" Heather asked and Jason stopped puttering around the kitchen to look concerned at us.

"I'm sorry." I said, still looking at the table.

"Whatever for dear?" Heather replied.

"For spending the night..."

"Darling," Heather laughed. "We have been expecting this. I was surprised that you two were able to wait so long. I was expecting to find you here about two weeks ago. I am sure that Karen was thinking the same thing. Now don't worry about it. Your clothes will be dry about the same time you finish breakfast."

"Western omelets okay?" Jason asked like this was a perfectly normal scene.

"Yes, thank you." Trent said looking somewhat more relaxed.

"I love that just tumbled out of bed look on you dear, but you will need something a little nicer for breakfast," Heather said smiling and taking my hand. "Come with me and we will see if we can fix you up."

She led me back up the stairs and into the bedroom across from Trent's room. She walked over to the closet and pulled it open to revel what looked like a complete wardrobe for me.

'Here you go dear, the clothes are your size, you will find lingerie in the dresser and the bathroom is prepared for you. Why don't you get cleaned up and changed and then we can have breakfast."

"Heather, you..."

"I set this up when we got back from the cruise. Unlike my son and husband, I have been expecting to see you at breakfast, and long before this. You are welcome to spend the night anytime you and Trent chose. If he brings you over and you don't have your car here, just hang that little bag you found on the door back on the handle and I will know."

She stepped out of the room and closed the door behind her, leaving my standing there open mouthed at her generosity. I stripped off Trent's shirt, and hopped into the shower. The bathroom was indeed completely stocked with everything I needed and in a matter of moments I was completely refreshed and ready to dress.

The closet held dresses, skirts, blouses, slacks, shoes, and coats of every possible. The dresser had more lingerie than I would ever need, and one look at them told me that they were all top quality and pure silk. I had not noticed when I dressed in Trent's room, but the pair of panties that Heather left for me were also silk. The feeling of silk sliding up my legs and settling around my hips, cradling my clit was electric. I picked out a white silk blouse and a gray skirt but stayed barefoot and headed back down to breakfast.

That set tone for the rest of the year. I didn't spend every weekend sleeping in his bed, but having sex there or at home was a lot more comfortable than in the car.

Graduation was the usual pomp and circumstance. I graduated with honors and my gown had the gold sash to show it. Trent had decided to go to USC for business and I breathed a great sigh of relief knowing that he was safe.

My dress for the occasion was a simple white summer dress and two inch heels. I was not going to wear too much under that gown. Graduation was held in the stadium of the school on a crystal clear sunny day.

We filed up the stage alphabetically and each person was announced, along with their choice of school, if they had one and whether they had graduated with honors. Kevin was the valedictorian for the occasion and he gave a wonderful speech about hope for the future and the wonderful memories of our time at school, the sadness of leaving and the eagerness of taking on new challenges. Afterwards caps thrown in the air, gowns open and ties removed we made our way out front for the traditional graduation gifts.

Mom and Susan were waiting for me out front and led me over to a new red Volkswagen Passat convertible. I screamed in delight and flung my arms around Mom and hugged her tight.

"You earned it." Mom said hugging me back. "And you will need something a little nicer in LA."

Trent slipped up behind me with his parents and looked at the car.

"Nice ride." He said putting his arm around me. "But mine is still nicer." He oofed as I elbowed him in the ribs.

"Be nice, or I won't take you for a ride in it."

"Yes you will, or I won't share my present with you." He said loftily.

"And what might that be?"

Jason laughed behind him and handed me an envelope.

"Don't worry Janie, he has to share, your name is on it too."

I looked at him confused and he just pointed to the envelope. I opened and a piece of paper slid out into my hand with a key attached. I turned it over and read an address on it in LA.

"Jason..." I started to say.

"Now, it isn't what you think." Heather said with grin. "We have leased a house for you while you are in school. We were going to do this for Trent anyway and since you two seemed to have developed an affinity for sleeping together, it just made sense give you your own key now to save time."

I blushed and looked at the ground for a second as I remembered the first weekend we got caught.

"You got us a house?" I stammered.

"Just for the next fifty years or so." Jason laughed. Heather slapped his arm.

"Only for while you two are in school." She corrected. "It is fully furnished and we have possession now. I know that you will want to make it your own, but you can move in any time. I thought it might be a nice place for you to stay during your photo shoot next week."

"I don't know what to say." I said. "Thank you so much."

"You are more than welcome sweetheart." Jason said hugging me. "I'm just sorry that Trent has to go with me on a business trip that week or he would be with you at the shoot."

"Actually, it is probably better that he is going with you Jason." Mom put in. "I don't think he would like to see his girlfriend being photographed for the rest of the world to drool over."

I looked at Trent and saw the concern in his eyes as it hit him. I was not just going to belong to him anymore. Millions of other guys were going to see me and probably want me. I got a thrill of excitement along with my concern for him.

This was going to be an interesting week.

DMaster_14
DMaster_14
1,066 Followers
12
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
6 Comments
AnonymousAnonymousabout 9 years ago
Nice, but....

I like this story but the fact that Janie's mom and sis are playing dress up with a emotionally damaged person to begin with, it makes me cringe and frown.

I wish they were mute in the story along with the sex crazed friends and bf's rents.

AnonymousAnonymousabout 12 years ago

Each time I read the story of Janie and Trent, one of the best story series in the whole Literotica I get an even huger and uncontrollable urge to complete my own ongoing sexual transition, become a girl like Janie and find myself a boyfriend like Trent. It has become so clear, so obvious to me that some men unsuccessful and unhappy with life like me and Janie were never meant to be men and the moment we find our real sex everything changes and we can finally conquer the world and our own lives. Janie is my greatest idol and inspiration and I am already expecting for Trent to propose to her, after all they are already living as a married couple.

All right, enough !! I have to send a feedback congratulating the author for his work !

AnonymousAnonymousabout 12 years ago
good

i would like to see you start a different but similar series

AnonymousAnonymousabout 12 years ago
great story development

Good plot lines and progression. For some reason I started getting the feeling Janie was going to get the urge to go "all the way" with a gender transformation. She is truly loving being as female as she can be.

Great job!

AnonymousAnonymousabout 12 years ago
AS always!

This was a great read as always but it seems the story is moving sort of fast now. I guess the end will be soon in coming. But it has been one heck of a story. I will really miss this story when it ends.

Thank you so much for the read.

Tim

Show More
Share this Story

Similar Stories

Drink or Dare A drinking game with new friends changes everything.in Transgender & Crossdressers
My Feminine Side Guy becomes a beautiful sexy girl.in Transgender & Crossdressers
A Big Side Effect A girl's medicine causes a strange...growth. And urges.in Transgender & Crossdressers
My Big Sister His older sister has a few surprises.in Transgender & Crossdressers
His Teacher, The Transsexual A young man ends up very close to a teacher with a secret.in Transgender & Crossdressers
More Stories