First Time Fucking My Best Friend

"Don't go inside," she said.

"I promise. I'll just slide it up and down, and rub it against your hole. It'll feel real good."

"Uhhh ... I'm not sure ..."

"OK, here's the dare - take it in your hand. You rub it around, and I'll just stand here rubbing your big clit."

Still bent over on the towel, she reached behind with one hand and grasped the base of my rock hard shaft, then started to rub the cockhead up her slit. I rotated my wrist around the helmet of her big clit, and she gasped as simultaneously my cockhead slid over her hole and upward.

"Does that feel good on your pussy hole?"

"Oooooh ..." She slid my cockhead back down between her cheeks, lingering this time as the tip touched her pussy opening. "Uuhhh," she said, looking surprised, her mouth open. I kept working her clit. "Ohmygod ... uhh ... so good ..."

"Keep sliding it. Up. Down. Up again ... now circle it around your pussy hole."

I got between her legs and nudged them wider apart, then used my other hand to work her balls.

She groaned. "Oh, fuck, that feels good."

I put pressure on her left thigh, and whispered in her ear, "Put your knee on the counter."

"Uhhh, why?"

"It's hard to reach your balls like this. I want to make you feel good." I leaned over and kissed her on the cheek.

"Kiss me," she whispered.

Our lips tentatively touched. What felt like an electric jolt ran through my nerves. Her pupils widened.

"Take control," she said.

"You sure?"

"I want to be a good girlfriend for you."

I kissed her a bit longer, my cock stiffening even more when she slipped the tip of her tongue between my lips. Then I stood back up, and she let me lift her leg onto the counter, leaving her butt cheeks opened and waiting, wobbling a bit with just one leg on the floor for balance. I grasped the base of my rigid shaft and began short strokes back and forth over her hole, the tip of the head catching the rim each time on the way up for a brief moment, then sliding free again. "Do you like that?"

"Oh, fuck ... oh ..."

"Do you want me to stop?"

"Please don't. Please."

"Wait a minute." I kissed her neck again, then planted kisses down her spine and then onto her buttocks while sliding my hands up her inner thighs. I kissed my way back up her spine. She shivered and jiggled her bubble butt, inviting me to continue.

I stared at the hypnotic motion of those globes bouncing around. Daay-yam.

She gasped as my cock slid down her asscrack and started rubbing circles around her well lubricated asshole, teasing her. After a couple minutes of this, she started wiggling her hips, trying to get my cock centered on her puckered button.

"Can I push a little harder? I promise I won't go inside."

"Do it. You're in control now."

"Say it. Say you want it."

"Please. I want to make my boyfriend feel good."

I pushed harder against her tight pussy hole, pressing upwards, stretching the lip.

"Huuuh," she gasped. "God that feels good."

"Do you like being teased like this?"

"God, I love it."

I kept teasing her, playing catch and release with my cockhead and the upper part of her rim, pushing just hard enough to place pressure but not go inside. She started bucking her hips back at me, like she wanted more pressure.

"You can put just the tip inside," she gasped.

"Just the tip?"

"Yes."

"Say please."

"Please, goddamit. Please!"

I started pressing harder and harder, watching her face in the mirror, a look of surprise or shock on her face, like she couldn't quite believe that this was real, that she had consented to sucking my cock and then to being bent over like this, consented to getting my cockhead inside her.

"You're so tight," I said. "Relax. Let me in."

"Ow. Oww. Ohmygod. It's too big. It won't fit."

"It'll fit. Press back when I push." I grabbed both her hips and pulled hard. My cock bent from the pressure, hurting a bit, but I didn't care. "C'mon. Give your boyfriend your pussy."

She began panting, short gasping breaths.

"You can take it. Your ass feels so good against my cock."

Her eyes met mine in the mirror, her face grimacing with the pain, but her eyes loving me, wanting me. I kept pushing and backing off, letting her get used to it, but I couldn't get it in.

"Lemme loosen you up."

"OK, OK ..."

I lubricated my middle finger and pressed, and she made a shocked sound as it slipped in, her incredibly tight hole gripping it. She made sexy gasping and moaning noises as I fingerfucked her. After a few minutes, she said, "Please. Try again."

I wiped the finger off on the towel and positioned my cock on her pussy hole. I leaned in and my cock bent, and it felt close, like she was almost loose enough. I felt her shove her ass backwards at me and my cockhead slipped inside and her mouth made an "O" of surprise and maybe some pain, and "Yes," she said, "yes. Oh god. Yes."

I paused inside her. "Just the tip, like I promised." I pulled out. "Want me to stop?"

She looked over her shoulder at me while her hand silently answered, guiding my cock back into place.

It went easier this time, her hole starting to loosen, but still by far the tightest pussy I'd ever been in. I got my cockhead inside again, then started rocking, tiny motions in and halfway out. She made the sexiest sounds I'd ever heard before during sex, soft moans as I fucked her with just the head.

"Is this OK?"

"Oh. Oooh. Easy. Slow. Fuck. Fuck."

"Do you want me to ..."

"Fuck. Me. Fuck me!"

I grabbed her hips and started working the shaft inside as she moaned and thrashed and thrust back trying to get it all in. "More. Deeper. Fuck me, Robert. Fuck your girlfriend." She turned and looked at me in the mirror. "Please."

"Does it feel good?"

"Oh. Oh. So hot. Spank me."

I slapped her sexy butt lightly.

"Spank me!"

I slapped it harder and she cried out with pleasure. I grapped a fistful of her long hair and pulled her onto me, bucking for dangerous penetration, and she fucked back while making sexy squeaky animal noises and I got all the way inside, balls deep. I started to fuck her faster, her voice making noises urging me on, making it so hot.

I pulled out, teasing her. She opened her mouth as if to protest this betrayal of her wishes, and then I shoved it back in.

"Aaaaah," she said as my cockhead bottomed out inside her pussy, over and over. She grunted and gasped hard, watching in the mirror as my face scrunched up with pleasure. "Fuck my tight ass. Slow down. Oh, there. Aaah, fuck, that's my G spot. Yes. Yes. I love being your girlfriend. I love having you inside, fucking me." She watched and moaned and spread her legs wider apart, giving me her body fully, as I grasped her hips harder and picked up the pace again, slamming into her, spanking her.

"Take it," I said, gasping for air between words. "Fucking. Take. My. Cock. In. Your. Tight. Pussy!"

"It's your pussy. Your pussy to fuck."

It felt unreal - how did a married straight man like me wind up bending over my best friend on the bathroom countertop, grunting, grabbing her hips, and sliding my cock deep into her asspussy? I grabbed some more lube and resumed stroking and squeezing her clit, wanting to make her cum. I shifted my hands from her hips to her shoulders, getting more leverage, trying to jam it in just a bit more. "I can't wait. Gotta cum. Can I cum in your pussy?"

"Yes. I want you to cum in me. Shoot your cum in your girlfriend."

I groaned and stopped, trying to hold off a moment longer.

"Now!" she said. "Now. Don't stop." She started fucking herself on my rod, thrusting her hips. I let her take control, holding still.

"Fuck back, baby!"

I resumed plunging again and again into her, my thighs slapping against her ass.

She moaned like she was ready to cum too, so I took one hand off her shoulder and wrapped it around her clit, pistoning it.

"Yes. Oh god, I'm about to cum too," she said in this lovely voice husky with desire.

That sound of desire and lust put me over the edge ... "Aaaaah. Ohmygod, I'm cumming. It feels so good. Take it. Take my cock." I bucked against her again and again, riding the waves of pleasure, shooting huge amounts of sperm in her. I felt her clit start spurting too, making a sticky wet pool on the towel, more than the cotton could soak up.

When she had taken the last of my cum inside her, I lay on top of her warm back, sleepy from the recovery. It felt so weird, but in a good way - how did I wind up on top of my childhood best friend, her - well, no, his - time to let the roleplaying go, so sleepy - his ass full of my cum, his face splattered with my sperm earlier, fucking him earlier like he was my bitch while pulling his hair and spanking his ass, having the best sex of my life? But I'd do it again - it felt so good to get to fuck someone so different from my wife, lean where she was curvy, tall versus short, kinky where she was vanilla. How the fuck do you keep up monogamy year after year when you crave variety? How does any guy pull that off? I stroked Harry's hair, kissed his shoulder blade, and whispered in his ear, "Mmmm, that was so gooood."

Harry looked at me in the mirror. Was that worry in his eyes? "Do you think we might - you know - do this again?"

"I'm fresh outta cum. I think I'm done for a while."

"That's not what I meant."

I thought about ducking the question, but Harry and I had never kept secrets from each other, starting from back when we were little kids tearing around the neighborhood on our bicycles causing trouble and leaving mild destruction in our wake. "I'd like to have a sexy girlfriend on the side who'll let me fuck her any way I want."

"I'm yours. Yours to fuck." He parted his lips, like he wanted a reassuring kiss so he didn't feel used despite my softening cock starting to slip from his ass. I felt him squeeze my shaft with his tight ring, like he didn't want to ever let go ...