The Girlfriend Whisperer Pt. 01

The Girlfriend Whisperer, Part 1: Jake and Carol

Carol is pressuring Jake to get married, meanwhile she uses Dante to relieve her pressures.

First a little about me, then I'll get to the good stuff. My name is Dante, I've been described as a kind of Don Juan type, my father was Spaniard and my mother was French, he married her because she was kinky and into ménage à trois, and he was a true lover of women, so I guess the stars aligned to make a tall, dark, and handsome man for the benefit of women. My feelings were pretty much ignored in the process, some people can't believe it when I say I've never had a girlfriend in my whole life, there is just something about me that repels that connection. My first crush broke my heart when I asked her out, she said, "you're the kind of guy I'd like to hook up with as a one night stand but not see myself with permanently." Ouch. But I've learned to accept my role as God's gift to women, and as they say it's better to give than to receive.

The first time I became "The Girlfriend Whisperer" (sometimes the Wife Whisperer) was by accident, and my friend really walked me right into it. His name was Jake, and he called me up one night, complaining about his girlfriend Carol. He was saying how she was pressuring him to propose, get married, and quickly have kids. She was 30 so I guess her biological clock was ticking away. He was just happy living a relaxed life, drinking beer, watching sports, and banging his girlfriend. He asked me to come over and drink with him so he could vent.

"Fine," I said, knowing that his girlfriend would be there since she hardly ever goes out. At least I could stare at her boobs and watch her walk around in short shorts while Jake complained about his life.

When I got there I was sad to see she wasn't there. We had some beers and I listened to him complain about a woman wanting to marry him (did I mention I can't get a girlfriend?). He turned on a baseball game (sports bore me), and we sat and drank like a bunch of depressed losers. Then suddenly, I heard a pitter patter coming down the steps. And there she was.

Carol had long, thick black hair, with very white skin. The contrast of her light skin and dark hair always intrigued me. She looked like some medieval maiden that might've graced the cover of a trashy romance novel. She had this tiny white tank top on with her double D boobs bouncing out of them, and little tiny shorts covering her big booty. She had a great hour glass figure. She didn't say anything to me when she saw me, I always felt there was some weird sexual tension between us, though I always felt that way around women.

"Hi, Carol," I said.

"Hi Dante," she said, almost as if it was a chore. She must've known I was there but was dreading coming down. That made me feel like shit, was I that repulsive to women?

"I hope you're not going to stay up all night drinking," Carol barked at Jake. "We have to go to my parents' house early tomorrow."

"Hmph," Jake grunted, looking over at me with an 'I told you so,' look. Jake felt smothered, almost like they were already married. Why buy the cow when you're already making payments on it?

I knew that Carol's sister was really hot, I had seen pictures of her. "Can I come too?" I said in a joking way. "Is your sister still available?"

"She's dating some Middle Eastern guy now," Carol said.

"Right," I said. "Hang out with us, drink a beer."

"No, I'm cutting back," she said. Jake made another grunt, his world was closing in and his girlfriend wouldn't even drink with him anymore.

"Worried about losing your figure?" I teased. "You're still killer."

Jake looked over at me with a raised eyebrow.

"What? You should be happy you got a hot girlfriend," I said.

"Move over," she said. Jake and I were sitting on the couch, on either end, but now she shoved me over. Her and Jake were on the sides of the couch with me in the middle. This was double awkward, now I was sitting a little too close to my guy friend and a little too close to her, and being in the middle was like triple awkward.

"So who's playing?" She asked, annoyed that sports was on.

"The Oakland pitchers vs the Cleveland...hitters," I joked.

"All he does is watch sports," she said.

"All she does is read books," he said. Carol was a book worm, she reads over 100 books a year, she once bragged.

"Maybe find a book on baseball and you guys can hit it off," I joked. Neither laughed. I was like the third wheel marriage counselor, except not getting paid. I nudged her a little bit, trying to make her cheer up. She had a frown on her pretty face. "Give me a little smile, girlfriend," I whispered to her.

She leaned her leg over at me, touching my leg very deliberately, I could feel my loins beginning to stir. Her naked leg, all the way up passed her thigh was tantalizing to look at. She was hunched forward a little, and her smooth white top of her breasts were open to the air, very slight blue veins visible as they disappeared into her tanktop. I could smell her hair was recently washed, it was frizzing up a little, but she had a miserable look on her face. I wanted to kiss her on the cheek just to cheer her up.

"It'll be okay," I said, I needed something to say, but my real intention was placing my hand on her thigh. I wanted it to seem like a "there, there," patting her leg, but instead touching her was the real goal. I kept my hand there, she made slight eye contact with me. She pushed her leg harder against me. She actually started to grit her teeth, almost like she was trying to hurt me by shoving her leg into mine. Some pent up frustration for sure. I couldn't help but burst out laughing.

"What the hell is going on over there?" Jake asked. "Do I need to separate you too?"

I have a, let's say, established history of hitting on my best friend Jake's girlfriends. Nothing ever happened before except for some sexual tension, but he never quite forgave me for it. At the same time he knew that was just my personality. He coined the phrase that stuck with me ever since, "don't leave your girlfriend alone with Dante," he once told a mutual friend.

Jake got up to get a beer. "You need one?" He asked.

"No thanks," I said.

"Okay so a 'yes,' it is," Jake said, grumpy.

"He's such a drunk," Carol said. Our eyes made contact. Now that we had a brief moment alone my demeanor changed. I looked at her lovingly. I brushed her hair slightly, something I wanted to do since she walked down the steps. I leaned forward a little, not sure if I was going to kiss her or not, then decided to just hang there, teasing her a bit. I waited for her to say something, she didn't. But she kept her eyes focused on me. I was hoping she'd make the first move but I wasn't so lucky, so I had to roll the dice and take the risk myself.

"I want to fuck you," I said.

She turned away, just as Jake had come back into the room.

"Ugh," I let out. He had thrown a cold beer right into my lap, and hit a very sensitive, erect part of me. "Thanks," I muttered. I opened the beer, knowing it would explode. It went all over Carol's legs.

"Sorry babe," I said, wiping the beer off her leg, another excuse to touch her.

"You jerk," she said, and got up and stomped upstairs.

"Smooth," Jake said. "You can move over now."

I went to the opposite end of the couch. Did I piss her off? Was my joke too much? I pulled out my phone, I had Carol's number in my contacts (something that made Jake nervous). I texted her,

"You mad?"

"No." There was a pause, and then,

"I want to fuck you," she texted.

Oh shit, now I've done it. Jake was watching the game, unaware of what I was doing.

"Send me a nude," I texted.

With minor hesitation I received a text. I couldn't believe it. She was in her bed, completely naked, holding the phone over her and showing me all the goods. Her huge natural boobs and her trimmed black bush. She had a slight smile on her face, not much but just enough.

"Take one of you rubbing yourself," I texted.

"I don't like doing that," she said.

"Pretend it's me doing it" I replied.

The text came quickly. She had her hand on her crotch, with a not so happy look on her face. I smiled at her compliance and even though she was faking it seeing her touch herself was turning me on.

"Get Jake out of here," I texted.

"Jake!" She yelled from upstairs.

"What!?" He yelled back.

"Can you go to the store and get me some Aspirin? My head hurts."

"Ugh, my head hurts," Jake mumbled. "Fine."

I froze on the couch as he stood up. This was really happening. He looked over at me, expecting me to get up, too.

"Right, I probably should get going," I said.

"Thanks for letting me complain," he said.

We walked out of the house and separated towards our cars. I waited in my car until he drove by. When he was out of sight I doubled back towards his house. They never locked their doors, and I walked in and ran upstairs. I knocked on the bedroom door and then opened it. Carol was under the covers, but when she saw me she threw them aside and was still completely naked, spreading her legs out before me.

"How long will he take?" I asked.

"10 minutes."

Talk about pressure. But luckily our sexting had already warmed her up. I moved to the bed and she squirmed a little in anticipation. I placed my hand on her crotch and she was wet. I slid my pants off, I was only half erect. I kissed her passionately. Her hand went down and rubbed my shaft. It felt incredible, but she surprised me by wasting no time and sliding my cock into her. Her wet pussy got me erect the rest of the way.

She started moaning with pleasure. I thrusted in and out of her powerfully. I then picked up steam until I was going full speed on her, grabbing her large breasts and squeezing them tight. I held her tight to me like she was a coveted possession. She dug her nails into me and I could feel her frustration and tension being taken out on my back. I knew they'd leave a mark, but it just got me to pound her pussy even harder. My dick was getting harder and harder inside of her. She was tightening up around my shaft. I was now going full blast on her as she screamed with pleasure. I knew I was close to orgasm. I couldn't hold it any longer.

I buried my face into her lovely hair. I pushed into her as far as I could and her mouth opened wide as she orgasmed. I exploded into her. Her legs were convulsing as I groaned with pleasure. I couldn't move under the force of my own orgasm, I was vulnerable and helpless. I held myself in her as I squirted every last drop out and into her pussy while she kissed me lovingly.

When I finally got control of myself again, I started to panic.

"How long was that?" I asked.

"I don't care," she said, laying back in ecstasy. "Just lay her a sec with me."

I wanted to flee, but she wrapped her arms around me and shoved me into her breasts. A part of me was worried I'd get caught, another part of me was breathing into her boobs. She was still reeling from the orgasm, as she rubbed my back, running her hands over where she had just previously scratched her nails into. For a brief moment I closed my eyes and was able to relax, I could've stayed like this forever, laying with this beautiful naked woman I had just satisfied. But she wasn't mine to hold. I decided that was enough time.

I grabbed my clothes off the floor and changed quickly. She was still laying spread eagle, I took one last adoring look at her before walking out.

As I was going down the steps, I saw Jake walking up the porch. "Oh shit! That was less than 10 minutes." I ran to the back door. I opened it just as he opened the front. I timed it so I closed the back door at the same time as he closed the front, to mask the sound. I ducked as I walked passed the window.

I got into my car, breathing harder now than when I cummed just a moment ago. I got a text notification. Carol had sent me a creampie pic, a close up of her crotch, with my cum dripping out of it.

"Are you still naked? He's home," I texted, assuming Jake was heading upstairs.

"I'm under the blanket, he doesn't know," she texted. "Thanks for the Aspirin, that really helped my headache."