First Anal

Today is the day. Today you were going to have sex for the first time. And it'll be with a man. If it were anyone else, like your other friends Mike and Tony, you would have turned them down in an instant. But not Bob.

With how often the two of you are hanging out this summer, he doesn't even bother locking the door anymore, and you make your way to the kitchen for a soda to loosen your nerves first.

"Bob! I'm here!"

"Good Morning," he gracefully sweeps downstairs, already all dressed up. He looks much better this time - with the dress somehow fitting looser around his frame. More importantly, he is now walking confidently in his heels, the result of obvious practice. Even his A cup bra seems to jiggle on him, probably stuffed with something. "Would you like a bowl of cereal?" He asks as he bends over to open the refrigerator, giving you a peek of the panties he's wearing underneath the white dress.

You can't help but feel that he's doing it on purpose - the way he shows off his 'cleavage' when pouring milk, and then the way he angles his hips when he washes the dishes. Eventually, you can't take anymore.

"I want you now!" You aggressively bend him over the couch's armrest as he lets out a small yelp.

Pulling up his dress, you give his perky ass a light spank for the way he's been teasing you. "Naughty girl! You've been teasing me on purpose, haven't you?"

"Oh, no, I would never even think of that!" He innocently exclaims. SPANK!

"Good girls don't lie like that. When they do, they get spanked." You grind roughly against his legs, your erection pressing into his pink panties.

"I'm sorry! I've been a bad girl!"He moans as he humps back, his own penis threatening to rip the tight underwear.

"Yeah, and how are you gonna apologize?"

"With this," he hands you a condom. Dirty girl really did have this all planned.

You tear it off as your friend keep humping, and then start to unbutton your jeans. When your clothes are gone, you slip the rubber over your erect dick and pull down the only thing in your way.

You gasp in surprise as you see Bob's ass is completely shaved. There's not a single hair there, nor is there anything on his balls, the little sack hanging tightly from beneath. Marveling, you trace your fingers everywhere, then, unable to resist, you give him another spank.

"Owie! What was that for?"

"Your ass is just too smooth. I couldn't help myself." You grin at him as you slowly rub his anus with your thumb.

Next, you stick your index finger in your mouth, getting it nice and wet, and then bring it over to his cute butt. Slowly, you stick it inside, gently pushing forward until it's all the way in. Bob moans in delight, burying his head in the sofa, leaving all you can see as a mop of blonde hair. You flex your finger in and out, making sure to rub his prostate on every stroke. When it's time, you add your middle finger to the mix, stretching his tight hole with forbidden sensations. Soon, he's humping back into your hand, his little dick fucking the couch as he does so.

"I think you're ready," you whisper as you remove your fingers and press up with your cock.

"Mhm," he breathes, and then you push in. Slowly, gently, you stretch Bob with your girthy tool, giving his virgin pucker time to adjust. He's a bit loose from the finger fucking you just gave him, but it's still an effort on his part. Deeper and deeper you go, spoiling yourself with sensations you've never felt before. About half-way in, his butt clenches tight around your cock, and you take it as a sign to stop.

"How's it feel?" You ask.

"It's a mix," he admits, turning his made up face towards you. "You're all the way in, right?"

Ordinarily you would have burst out laughing, but instead you playfully bite his ear as you whisper "half-way." That triggers another butt clench of surprise, and you have to struggle not to cum then and there. Instead, you massage his cheeks with your hands, helping him loosen up while you slowly push yourself further in. Bob moans in pain when you're three quarters inside, and though you slow down a bit, you do not stop. You're 100% determined to fully burry yourself in his virgin ass.

After what feels like an eternity, your hips collide, and you can finally feel the tip of his dress teasing your legs.

"There, there. It's over."

He nods, but it seems to take all his effort. "Just go slow," he pleads. You reach over and wipe a tear from his pretty face. Unfortunately, it took a bit of eyeliner with it as it came down, and now he has a silly streak of black falling from eye to cheek.

Disappointed with how much you're hurting him, you decide that you'll try your best to make sure he enjoys this. You pull your hips back - not the whole way, maybe just one or two inches - and then push forward again. This way he gets the pleasure of his prostate without the pain of getting banged. And you get to enjoy the warm confines of his ass, muscles still furiously squeezing, trying to **** you out. You're thankful for the high heels he's wearing, as they **** his hips at a steeper angle, making the whole thing much more comfortable. It's not long before you feel an orgasm arriving.

"God, your ass is so tight, Bob!" Your voice cracks with pleasure as you **** yourself to keep your slow pace. "I'm gonna cum! I'm gonna cum in your ass!" You dick spasms inside your friend, the rubber collecting all your seed.

Exhausted, you collapse on Bob, getting a face-full of his long hair. Taking deep breaths, you notice a hint of perfume coming from his neck.

Although you could stay like this for hours, you know silent Bob needs to recover as well. Gently now, you pull out as his ass quickly tightens up. Kneeling down in front of your friend, you lift his face in your hands.

"You alright? You haven't said a word." When you speak, gone is the rough tough guy 'bro' voice you always use. Instead, your sound is now one of genuine concern.

"I'll live."

"That bad, huh?" You brush the hair behind his head, trying to get a better look at his expression.

"I'm just glad you're happy." He manages a smile. That's so nice of him to think of my pleasure first. You leave him be as you dispose of the condom and clean up.

Bob goes upstairs to change back into his ordinary clothes, but he says he's too sore to do anything besides watch TV, so that's what you do for the rest of the day. When you head home, together you decide on the next challenge.