Making a Woman Out of You

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A guy's best friend helps him with his fetish.
1.5k words
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Shelbey and Joey were hanging out at his house. Joey was a normal-looking guy with brown hair, and Shelbey was a taller, somewhat gothic girl. Joey had recently found himself to be bisexual, and he and Shelbey had just gone out to buy a vibrator for him to try out.

"Do you like it, Joey?"

"It's awesome, Shelbey! I can't wait to try it out."

The vibrator was fairly small and pink, the perfect size for Joey's virgin ass.

"I can't stand this waiting, though. I wish I could try it out now."

"Well, you could." Shelbey grinned to herself.

"But the shower is taken right now. I can't use it."

"Oh. Well...I guess you'll have to wait then." Shelbey laughed to herself and smiled. "You'll be okay, won't you?"

"No. I'm way too horny. Ugh, this sucks. Maybe I could....do it in here? You wouldn't have to watch. You could even go to another room." Joey blushed furiously.

"Sure. I don't even care, I don't need to go to another room."

"Uh....really? Are you sure?" Joey looked at his feet.

"Yep. Go ahead, do what you need to do." Shelbey smiled to herself as she watched Joey take off his shirt and pants, only to see a tent in his boxers.

"My, you're already hard, aren't you?" Shelbey giggled. "I guess you are horny."

"Shut up. I told you I was!" Joey blushed again. "Could you turn away now? I'm kind of embarassed."

"Oh, alright." Shelbey looked disappointed and turned away.

Joey pulled down his boxers, and took out his penis. He started to rub it a little bit, still feeling somewhat uncomfortable. "This is kinda awkward."

"Don't worry about me, hon. Just keep going!" Shelbey kept her back turned.

"Alright.." Joey squirted some lube onto his hand and started to rub it. He moaned a little as he started.

"Well, aren't you going to use that vibrator?" Shelbey laughed. "You left it over here."

"..Oh. Can you throw it to me?"

Shelbey laughed again. "Nope. You have to come over here and get it."

"Shelbey! That's not fair." But he got up and walked over, blushing furiously. As he got over there, Shelbey got a perfect view of his dick, fully enlarged.

"Oh wow. I never knew my best friend had such a nice penis." Shelbey giggled.

"Stop teasing me, you aren't funny." Blushing more, Joey grabbed it and sat down.

"So how do you...use this?" Joey still blushed.

"I dunno. I've never tried one before. Play around with it."

"Do you really have to watch the whole time?"

Shelbey grinned. "Yep. I've always wanted to watch this. Go for it!"

"Alright then.."

Joey rubbed his penis again. He grabbed the vibrator and turned it on. He rubbed it around his legs, then over his penis head. He touched it under his scrotum, then around the outside of his ass.

"This feels so weird...it's really awkward." Joey kept rubbing thevibrator around his hole.

"Well, why don't you put it in?"

"I dunno. I feel weird about this."

"Would it make you feel better if I took off my clothes too?" Shelbey smiled at him.

"Uh...." Joey was surprised by this. "Don't you have a boyfriend?"

"Yeah but he won't mind. It isnt like we'll be having sex or anything."

"Well...I guess."

Shelbey slid down her skirt and tossed it to the floor. She pulled off her top and tossed it too.

"Do you like my bra and panties?" She was wearing red and black underwear that accentuated her small curves.

"Um...yeah."

"Wow you're really hard again." She giggled. "Should I take off more?"

"Um...sure."

She unhooked her bra and let it fall. "How are my boobs? They're kinda small but boys seem to like them."

Joey continued to rub his dick and rub the vibe over his ass.

"Alright, now for these things..." She slid down her panties slowly, then giggled to herself and threw them at Joey. They landed right on his cock. Joey blushed furiously as his penis grew even larger.

"Shelbey! Why did you do that?!"

She gigled and said "I thought you'd appreciate it!"

She sat down next to Joey with her legs wide open, giving him a full view of her nudity.

"There. Now you have something to look at. Put it in already!"

"Why are you in such a hurry?"

"Well it's really hot. I want to see you shove that vibrator deep in your manpussy."

"...Alright."

Still staring at Shelbey's petite body and shaved vagina, Joey slowly began to push the vibrator in.

"Oh god...this feels really good."

"It look sooooo hot. Keep going!" She started to rub her clit a little bit.

Joey pushed it in deeper, then turned it on. "Wow..."

He rubbed his dick slowly at first, then sped up a little bit. Watching him, Shelbey rubbed her pussy faster. "Keep going...ohhh it's SO hot. Fuck that manpussy!"

"Oh god, I'm going to come soon!"

"Here, you can come on my boobs if you want." She climbed on top of him as he kept jacking.

"Oh god, Shelbey...." She put her hand down and started working the vibrator in and out of his ass.

"Oh god, I'm coming!"

She braced herself and slid the vibrator in deep as his cum came shooting out all over her boobs.

"Oh god...that was the best thing I've ever felt. Thank you, Shelbey."

"You aren't done yet, are you? Didnt you tell me you wanted to see what cum tasted like?"

"Um...yeah...?"

"Well, lick it all off of me then. If you do a good job I might even have a surprise for you." She winked at him.

He licked his cum off of her boobs untli it was clean.

"I see you're getting hard again already! But how about we try something new?" She reached into her bag and pulled out a strap, a dildo, and some clothing.

"Uh...what is all that for?"

"Oh you'll see. Stand up for a minute."

He stood up and she grabbed a bra out of her bag. She put it on him. She took panties out too, really slutty silky ones.

"Lift your leg up for me, hon."

He did. She slid the panties up.

"Now the shirt and the skirt!"

He put those on too.

"Now you're a pretty girl, and you are all mine."

"This feels kind of weird...."

"That's probably because your cock is coming out of the panties." Shelbey giggled. "Now lay down on the couch and just relax..."

He laid down. She took the strap on and set it up, then slid it on.

"Now, your best friend is going to fuck you. Are you ready?"

"...Yeah. But go slow, okay?"

"Don't worry, I won't hurt you."

She rubbed the strapon around his inner thighs, and over his balls and ass. She lubed it up, then put it at his entrance, pulling his panties aside.

"Now, I want you to tell me."

"Tell you what..?"

"I want to hear how much you want me to fuck your pussy."

"O...Okay...."

"Say it!"

"I...want you to..." He mumbled.

"Louder."

"I want you to fuck my pussy." He said under his breath.

"Still not loud enough!"

"Fuck my pussy! I want my best friend to shove her cock deep into my pussy!"

"That's more like it!"

With that, she slid it in. It went in easily, but it was a tight fit.

"Now I'm really gonna fuck you, you little slutty girl."

She started moving in and out of him. He moaned a little as she started going faster. He grabbed her boobs and massaged them as she fucked him.

"Oh god Shelbey, I'm cumming.....I'm gonna come!"

"Wait, don't cum just yet. We're not done."

She slid out and slid off the strapon.

"Now it's your turn."

"Wait...really?"

"Yes. You get to fuck your best friend now."

"You know how much I've always wanted this right?"

"Yes, yes. Now just fuck me already if you want to so bad."

"Okay. I will."

He took his rock hard cock, and started to slide it into her pussy. It was the tightest pussy he'd ever felt. She started riding him, slowly at first.

"Oh god, Joey. Your cock is so nice."

"Your pussy is even nicer."

She started to ride, in and out, faster and faster.

"Oh god, Shelbey. I'm almost there. I should pull out soon..."

"No. I want you to stay in me."

"But I'm going to.."

"I know. I don't care. Come inside me. Fill me with your cum."

He fucked her faster and faster, until he exploded inside her. She came at the same moment.

"Oh god, Joey.....Thank you. That was amazing. I needed that."

"You were amazing too. I should be thanking you."

"Here, one last thing...You wanna taste your cum?" She grinned.

"Of course."

She climbed up and sat on his face. He licked her pussy clean until there was no cum left.

"Problem solved, right? How did it taste?"

"Pretty good, actually...."

She started putting her clothes back on.

"Maybe next time we'll have to try it with a real man." She winked at him.

"I love you, Shelbey."

"I love you too, Joey."

She kissed him on the lips, somewhat forcibly. "I love you as a woman, and a man. But I have to leave, I have things to do. We'll have more fun another day, okay?"

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  • COMMENTS
6 Comments
AnonymousAnonymousalmost 12 years ago
dressed

omg sittin here dressed in womens clothes started readin this amazing story got so hot had to masterbate and fuck my manpussy with my vibe want to read more and get fucked by a woman with a strap on fuck yes and mayb her bf or husband I M me at cowboy5548 yahoo instant mesgr

AnonymousAnonymousalmost 12 years ago
hot

love to see more. I hope you keep the focus on his and shelbey's relationship.

james_38671james_38671almost 12 years ago
hot

can not wait for some more of this one

desireethtttvdesireethtttvalmost 12 years ago
loved it

cant wait til you get your first real cock

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