Brotherly Love, Sisterly Love Ch. 02

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

"REBECCA"

I was looking for Chad Taylor, the school's most popular guy and boyfriend of our host, Vikki. Earlier that evening, I had given Chad, dressed as a cowboy, a great blowjob but he had run out on me just as I had revealed my own cock to him. Now, I was looking to finish things off with him. Sure, the gangbanging downstairs had been fun, but I could tell that Chad had really wanted me in spite of his inhibitions and a hunky stud like that was just what slutty Rebecca wanted too.

I ran into him on the stairs and, telling him "We've got unfinished business", pushed him into a large, empty bedroom. I pushed him back onto the bed and sat astride him, kissing him all over.

"Get off me, freak," he said, "I told you I don't want anything to do with you."

"Your cock is telling me different," I said, pulling it already semi-erect from his jeans and sucking on it to get it even harder, "Look, it's harder than mine!" I said, lifting my skirt and pulling my white thong aside. I couldn't help tormenting him about how it was really a guy that was turning him on so much.

"Just go away, ok?" he said, becoming a bit desperate not to show quite how aroused I was making him.

"How about you just do what I say and we'll both have a great time. Or maybe I'll just tell your girlfriend all about how you got a crossdresser to suck you off."

Well, that seemed to shut him up, although the fact that I then moved up to sit on his face probably helped. Without me needing to tell him, Chad began to eat out my asshole, really turning me on as his warm tongue thrust inside me, making me wonder what his cock would be like. As he became more eager, eating me out as he would his girlfriend's pussy, I delighted in reminding him what he was tasting.

"Mmmm, your friend Phil sure does have some tasty cum, doesn't he?"

I could see this was only making Chad's cock harder and I smiled to myself. Maybe he would like something else Phil had enjoyed. I got off his face and told him to flip over onto his front. It was amazing how pliable he had become. I had spent eighteen years as an ordinary guy but I had never yet used my dick to fuck a single person. Well, now I was going to take my chance and do it to this very masculine man. I propped him up with a pillow under his crotch and pushed my dick inside him. The stimulation of his ass on my cock was so amazing, it's grip so tight that I came practically straight away, filling his ass with cum and spurting all over his ass cheeks and back too.

I hoped he would last a little longer in me. Lying back on the bed, I opened my white stockinged legs and wrapped them around his waist, pulling him towards me. He no longer needed my persuasion and was only too happy to slip inside me with his cock already rock hard from the brief ass fucking I had given him. My own cock grew fairly quickly once more, sandwiched between our bodies. As he began to fuck my girly ass with abandon, he began to cry out.

"Oh Becky, oh yes. Fuck Becky, you're amazing! Sooo gorgeous, sooo tight. Better than any woman I've ever fucked!"

"Really?" came a voice from just inside the room. Our host, Vikki, dressed as a cowgirl in a plaid shirt tied across her breasts and tiny denim hotpants, had come to look for her boyfriend and had found him fucking the ass of a pretty blonde nurse. Her anger was only enhanced as she came closer to see that not only was I not all woman but the cum dripping from her boyfriend's ass suggested that he had hardly been all man this evening.

"Oh, so that's the way you like it is it? The I've got something for you," she said, "Don't move."

She left the room and a worried, emasculated Chad remained in place, his hard cock deep in my ass and my cum leaking from his. A few minutes later, Vikki returned. Still in her cowgirl hat and pigtails with the plaid shirt barely covering her admirable breasts. The daisy dukes were gone though, replaced by a huge eight inch rubber strap-on. Nor was she alone. She seemed to have brought the whole party with her, or at least all the hot girls, most of the guys were probably still downstairs fucking my sister, or each other.

"Well girls," said Vikki, "Do you wanna see the kind of man that Chad is?"

She walked over and thrust her strap-on into her boyfriend's ass so hard that he in turn pushed even deeper into me, causing us both to gasp with pleasure. With her girlfriends egging her on, this cute cowgirl proceeded to ride her cowboy boyfriend's ass, squelching into my cum that was already there. Chad was humiliated, red faced and tearful, but because of his girlfriend thrusting her strap-on up his ass, he couldn't help but remain hard and continued to fuck me. I, for one, was becoming quite an exhibitionist slut this evening and loved the audience of beautiful girls. I grinned at them, moaned louder for their pleasure and began to jerk my cock off for them to see. It didn't take much of this to cause me to cum all over my latex nurse's dress and my cowboy lover's chest while Chad filled me once more with his own cum.

As I left the room, Vikki still wouldn't let up, fucking her boyfriend even harder for punishment and for the delight of the watching girls for whom Chad would never again be the same specimen of masculinity. I found Rachel in the audience, he ripped and cum soaked costume like mine rearranged to be as presentable as possible. We decided to go home, it had been quite an evening with a lot of new experiences, not least our feminine selves having our first time with other men, fucked like real girls not just by each other. Not only that, but we had showed others how great it is to be fucked.

As we left, we decided to look in on the football guys and were pleased to find them still at it. Now the centre of their attention was a tall, striking girl in a whorish red wig and a very tight, revealing cheerleader uniform that seemed a couple of sizes too small for her. Even in the long red wig, her mouth in matching scarlet lipstick an "O" of delight as another guy violated her ass, her face was familiar. We had last seen it behind a Batman mask. I looked over at Rachel and my sister giggled.

"I found a game girl willing to do a costume swap," she smiled, "And now football stud Phil really is team slut Phoebe!"

I smiled. It sure had been quite a party, and not just for the two of us. Still, we had a couple of days before our parents were supposed to get home and that was plenty of time for Rachel and Rebecca to have lots of girly fun.

END OF PART TWO

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
17 Comments
AnonymousAnonymousover 3 years ago
nice story

It was a well written story

and here is a thought for chapter 3 why fast to the 4th of July

and a family trip to a family beach front Cottage -- Cabin and still more chance

full fill their lustful hunger,,while working on their tan lines.

And or a end of Summer Labor day weekend pool party??

AnonymousAnonymousover 5 years ago
We need more of the Adventures of Rebecca, and Rachel.

This has always been a fantasy of mine. Ever since I reached puberty, and began crossdressing I have wished for a little brother, or a twin brother who I could play dress up with. I imagined we would do each others hair and makeup; we would help dress each, then undress each other, and suck each other's little needle dicks until we flooded our mouths with fresh hot sticky cum. Then we would French kiss until we were ready to cum again. I used to try to get my younger cousin to play dress up with me, but he was having none of it. He would not even let me get into his pants, and he came from the well-endowed side of the family., and I would promise him the best blowjob ever.

AnonymousAnonymousover 6 years ago

I want more.

AnonymousAnonymousalmost 8 years ago

Can we get more?

AnonymousAnonymousabout 9 years ago
more!!!

I can't wait to see what the sexy twins get up to next

AnonymousAnonymousover 10 years ago
Omg please write more

I know it's been like 6 years but this story is just incredible. So so so so hot. PLEASE PLEASE PLEASE PLEASE PLEASE PLEASE PLEASE PLEASE PLEASE PLEASE PLEASE PLEASE PLEASE PLEASE PLEASE PLEASE PLEASE PLEASE PLEASE PLEASE PLEASE MAKE ANOTHER CHAPTER TO THIS STORY!!!!!!!!!!!!

ComodineComodineover 11 years ago
So naturally.. only happiness

An idea so original and made ​​with such a natural pleasure to read this story becomes orgasmic ....

I don't think that adding a new chapter could surpass the excellence of the surprise effect

Thank you for post it

Kisses ♥

CACTUS462CACTUS462almost 12 years ago
WOW!!!!

awesome hot story jessie, please add to this, im soooooooo ROCK HARD RIGHT NOW , i/we need more please jessie

AnonymousAnonymousalmost 12 years ago
Simply amazing.

Can't wait to read more. This is such an erotic coupling.

FoxRainFoxRainover 12 years ago
epic

This story is made of win

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

Party Slut Never fall asleep at parties!in Transgender & Crossdressers
The Babysitter Babysitter guy becomes babysitter girl.in Transgender & Crossdressers
My Big Sister His older sister has a few surprises.in Transgender & Crossdressers
Changing Room Prank Mark and Greg help me discover myself with a harmless prank.in Transgender & Crossdressers
My New Trainer Workouts will never be quite the same.in Transgender & Crossdressers
More Stories