Sarah's Cherry

"Relax, hon. It's just a bet. Besides, this will be fun!" Samantha could barely contain her excitement as she led me from the living room back to her bedroom. I had just lost another poker hand, and this time we had started daring each other do to things instead of playing for money. I got dared to dress up in Samantha's clothes by her friend Julie, who had to play the last hand topless.

She and I had been best friends for the better part of the last two years, but had never gotten to the point of being intimate. Something always kept that from happening. I figured wearing her panties was probably going to be the closest I ever got to getting in her pants, so I semi-reluctantly went along with it.

"What size shoe do you wear?"

"I gotta go that far?!"

"Yup, panties, bra, shoes, hose, makeup, and even a wig. I've got everything you'll need... and we have to shave that goatee off, too!" she said, adding, "so, what size shoe?"

"I wear a 9. I don't know what that translates to for your sizes – maybe a 10 or so?"

"Actually, it's 11. And you're in luck because that's the size my stilettos are."

Fuck. Now I've gotta try to walk in those after everything I've had to drink.

Samantha went into her closet and brought out a black skirt and a pink silk blouse, then opened her underwear drawer.

"Grab whatever you think will feel best!"

With trembling hands, I rummaged through until I found a nice pink thong.

"How about this?"

She smiled. "Wonderful. I'll grab the matching bra," she said, and pointed to the bathroom. "Now go shave. You better look good when you get out, and I don't want to see any hair poking through the stockings later!"

After shaving my face, chest and legs I came out to find she'd returned to the living room. I finished taking off the rest of my clothes and started putting hers on. This was something new, I hadn't even considered doing it before and wasn't too sure how I'd feel. I knew it would be interesting when I started getting hard after pulling on the thong. It felt oddly comfortable and very arousing. I knew I had to suppress that urge, though, because Julie and Samantha were planning to inspect just about all of me.

Once I had put the clothes on, I went back into the bathroom to put on lipstick and eye makeup, then grabbed a long blonde wig. Sliding my feet into her 4 inch pink heels, I started out.

The reaction was better than what I could have hoped for. Samantha's jaw dropped. Julie gasped. But now it was really odd, because Julie's boyfriend Aaron had stopped by while I was transforming myself. The girls decided it was time to have more fun.

"Aaron, this is..." Julie paused, trying to find a new name for me. "Sarah. She's Samantha's cousin. Sarah, this is Aaron."

I smiled and nodded at him. He stared at my legs, muttering a hello.

We went back to playing cards, and I kept as silent as possible. I could pass physically for a 23-year-old woman, but there was no way I could trick my voice out. After about another half hour, Aaron went over and passed out on the couch. Once he was out, I asked Julie how long they'd been together.

"Oh, a few months. He was out with some buddies tonight and he got really smashed before coming over here," Julie said, smiling. "I bet we could really trick him, if you're up for it."

"What's on your mind? You want to make him think Samantha and I are lesbian cousins?" I asked. "I'd be ready for that!"

I could feel myself getting hard again at the thought, as the fabric of the skirt got tight.

Samantha answered quickly. "We could do that. But I want to see how good you'd be as a girl."

"Huh? How good I'd be?"

"Uh-huh. You look enough like one. Let's have Aaron decide who gives better head between you and his girlfriend. You owe me another dare, anyway," Samantha said.

I drank another beer quickly to try to get myself ready. Julie went over to Aaron, unzipped his shorts and pulled them off. She started running her fingernails over his cock through his boxers, causing it to spring to attention. He snored. Julie slowly pulled down his boxers, and there it was... about 6 inches long, thick, smooth, and nicely trimmed. I looked at, then at the girls.

"Go. Suck it."

I did as Layle said. I got on my knees on the floor in front of his cock, and leaned in. I started by licking up the underside, which is my favorite thing to have done. It felt hard and spongy all at once. I licked it a few more times, then grabbed the base of it and put as much of it in my mouth as I could. Aaron moaned and started waking up. Julie quickly started kissing him to keep him a bit distracted as my virgin mouth began working his shaft.

His cock felt incredible in my mouth, filling it up all the way to my throat. Most girls I had been with were masters at deepthoating, so I figured I'd try to remember what they did and relax, going almost all the way to the base of his cock. When I wasn't taking it all in, I was stroking his cock with my right hand, playing with his balls with my left, and occasionally sucking his sack.

Meanwhile, my own cock was nearly bursting through the skirt. I was incredibly turned on by Aaron's moans and reaction to the blow job that I hadn't noticed Samantha had left the room. After a few minutes, I felt my skirt being lifted up. I didn't care. I just wanted to make Aaron cum.

I stopped sucking for a moment, noticing the pink lipstick that had been left on his cock. Julie smiled.

"Sarah's good, isn't she?"

Aaron's reply was muttered... something to the effect of "fucking incredible" as I started sucking him again. Just as I licked a finger and started probing his ass I felt a warm liquid hit mine. I whipped my head around to see Samantha behind me with a strap on dildo.

"Wha-" was all I got out before she slid her toy inside me. The pain was so intense it took everything I had not to scream. She slowed down her rhythym and worked with me after that, and we began getting in sync.. she'd thrust, I'd go deeper on Aaron. But as soon as he looked up and saw Samantha fucking me, that was enough.

"Hold on Sarah.. I'm gonna cum!" Aaron yelled and grabbed the back of my head, forcing it down on his cock as he came. I swallowed as much as I could, and nearly simultaneously let loose with a load of cum of my own, which shot out onto the floor.

Aaron, luckily for me, never saw my cock and never knew who actually had blown him. He left about 10 minutes after that was over, and he and Julie moved to Arizona the next week. That happened 10 years ago, and I haven't heard from either of them since.

Samantha and I got married the next year and are still together, and still like to revisit that night, with everything but Aaron!