Second Chances Pt. 01

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

"Yes, that sounds great," I say.

"Well, there's a really amazing authentic mexican restaurant in the Glen's plaza, or there's an amazing BBQ restaurant with a mile high sandwich with every different kind of pork you can think of. There's also a great italian place and there's always the pub," he says.

"I could eat some BBQ," I say.

"Great, we'll have to go back to the car. It's up town," he says. He holds out his hand and I take it. We find ourselves in his car, which if I'm being honest is a little messy and rather beat up, but I don't mind. We pull into a place across from the old Chinese restaurant called Pig's Grill. As we wait in line, I take a glance at the menu.

"What are you getting?" I ask.

"Oh I'm definitely getting the Pig's Mountain Sandwich. It's got everything on it," he says.

"I might have to give it a try," I say.

"It's a lot to eat. Would you like to split it?" he asks.

"Yeah, that sounds good," I say with a smile.

He places our order and waits for our food while I get our drinks and grab a seat. He comes over a minute later with our food. He cuts the literal mountain high sandwich in half and hands the other half to me. "I hope you don't mind getting messy because this thing is a beast to eat."

I laugh. "I don't mind. I love some good BBQ."

He smiles. "Me too."

We dig in and of course I get BBQ all over my face. He's just as messy. We laugh as we get all sloppy.

"You got a little here," he says as he uses his hand to indicate its' all over my face.

"Yeah, you got a little all over too," I say.

"Here let me help you," he says as he reaches over with a napkin and gently wipes my face. I find the act very hot.

"So, do you know what everyone else has been up to since high school?" I ask.

"Not a clue," he says with a laugh. "Although I know Austyn's still in town. He's usually at the bar every night. We don't talk much anymore."

"That doesn't surprise me. Some people never change," I say.

"So, what would you like to do tonight seeing how the reunion's not until tomorrow?" he asks.

"I don't know. Did you have anything in mind?" I ask.

"Well seeing how the huge festival is going on, we could do some rides and listen to the local band playing," he says.

"That sounds like a plan," I say.

We clean up our mess and head back out to his car. He drives us back downtown and we head over to the carnival. After we buy some tickets, we try a few rides. We end up at a basketball game and he buys us a few balls and lets me shoot. After I miss the first one, he steps up behind me and wraps his arms around me, adjusting my hands. "You have to get your arm under you like this."

I have to admit it's very sexy the way he shows me how to shoot. I then shoot the way he shows me and I still end up missing. "Ehh, these games are rigged anyway."

We end up heading over to the park where they're playing music. We watch for a while before getting some dinner at one of the food trucks. We then split an elephant ear and a lemonade. We take a seat on the grass and listen to the music as it starts to get dark. I end up resting my head on his shoulder and he wraps his arm around me. Eventually we end up heading back to his place.

HIs place is rather bare with only the bear minimum furniture. "Would you like a drink?"

"Uh sure. What do you have?" I ask.

"I have coke, sprite and water," he says with a smile. "I don't have any alcohol. Been sober for 5 years now."

"I'll take a water," I say. "And that's awesome. I'm happy for you."

"Coming right up," he says as I take a seat on his couch. He joins me a minute later and hands me the drink.

"So... About sleeping arrangements. You can sleep in my bed and I'll sleep on the couch if you like," he says.

"I honestly don't mind sharing a bed. I feel comfortable around you. That is, if you don't mind," I say.

"No. Not at all," he says before taking a long gulp of his drink and nearly spilling it. I hold back my laughter.

"By the way, I had a great time today," I say.

"Me too," he says.

"You really have changed," I say.

"It took some horrible life moments to really force me to change," he says.

"That's usually how it happens. If I was never bullied, I probably wouldn't have been this successful," I admit.

"You really think so?" he asks.

"Oh yeah. As miserable as high school was it gave me the drive to become something better. I wanted to prove to everyone that I wasn't worthless. That I had value," she says.

"Well, you definitely proved that. For what it's worth, you always had value. You have such a strong sense of self. To endure all the crap we put you through and to come out stronger, it's truly inspiring," he says.

I feel the heat rush to my face. "Thanks."

Before I can respond, his lips are on mine. His kiss makes my body flush with heat. His hand caresses my cheek and I lean into him. We finally break apart and we're both catching our breath. I look at him completely stunned.

"Are you sure about this? You really want to have sex with a tranny?" I use air quotes around the slur.

"No, I want to have sex with Samara Nicholson. The girl I wish I dated in high school," he says, making my heart melt. I lean back into him and kiss him. We end up going to his bedroom, tearing each other's clothes off before we're in his bed. His hands are all over me along with his lips. I feel his tongue swirl around my nipple has he messages my breasts. My body heats up to a sizzling level. He has me roll over on my stomach as he kisses his way down my back. I feel him bury his face between my asscheeks as his tongue finds my back door. I moan out as his wet hot taster plunges inside me.

He grips my ass and spreads it apart as feelings of warmth spread through my body. Suddenly, I'm filled with his fingers and I can't help but bite down my lip as a moan escapes them. I hear him rip open a condom. I look back at him. "Wait. There's lube in my bag."

He gets off the bed and grabs my bag as I paw around for the bottle of lube. I wasn't sure if this was going to happen or not, but I came prepared. I hand him the bottle and he spreads the contents over his rock hard seven inches of man meat before getting my ass covered in it. He straddles my thighs once more and I feel the tip of his dick slide down the crack of my ass.

I grip the sheets as the head of his monster man snake pushes up against my sphinter. Pressure builds up before his cock plunges deep inside me. I let out a yelp and bite down on his pillow. Thank god he holds his dick there and allows my ass to adjust. I feel his lips press up against my back. His hand intertwines with mine. I can't help but notice the contrast between his pale ivory skin as it presses up against my dark chocolate hand. Our fingers lock together as his dick slowly sinks into me.

I lean back and meet his lips with my own. Slowly he starts to rock his hips back and forth and I moan into him. I can't find words as he fills me up completely. The only way I can communicate is with my lips on his. His other hand reaches down and cups my face as his thrust become faster. I find myself bucking back to meet them.

I feel myself brought to the edge of the abyss and I want to fall in as long as he's with me. He grunts out and slams into me as we both collide with an explosion of pleasure. Our worlds intertwine and why he ends, I begin.

He collapses on me and kisses me. We both are spent after such an intense moment. He pulls out and disposes of the condom before getting under the covers and pulls me into his arms. The way he kisses me is better than any dream I've ever had. The fantasies I had as a teen have become a literal reality. I'm just afraid it's too good to last.

If you enjoyed the story, please give it an honest review below. Leave any questions you have in the comment section.

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
10 Comments
AnonymousAnonymousover 2 years ago

I would love to read about a part 2 and see where it goes.

AnonymousAnonymousalmost 3 years ago

That was incredible and has me in tears. You have a way of writing that always manages to bring out my emotions and the stories are some of the best I have read. You are an incredibly talented author who seems to have a great feel for the kind of life that people want to read about.

AnonymousAnonymousalmost 3 years ago

une superbe histoire avec une belle morale..

j'adore et j'attend la suite avec empressement

phoenixcindersphoenixcindersalmost 3 years agoAuthor

Check out my profile for more information on Second Chances.

KirabangkokKirabangkokalmost 3 years ago

Oh wow. I really like how this is going. You asked for honest opinions, I am anxiously awaiting the next part. Definitely five stars

Show More
Share this Story

Similar Stories

Secrets and Surrender High school can be lonely, but shared secrets can help.in Transgender & Crossdressers
A Game of Basketball Star Basketball player loses his anal virginity to new girl.in Transgender & Crossdressers
"What Does She See in Him?" A high school boy finds the girl of his dreams is a bit more.in Transgender & Crossdressers
Unexpected Patronage Ch. 01 Nara shelters from a storm with an adorable red haired guy.in Transgender & Crossdressers
In Time for Summer A boy gets seduced by his "lesbian", packing roommate.in Transgender & Crossdressers
More Stories