Favorites Stories “How Big Are You?”

How Big Are You? Favorite Stories

“Excuse me, how big are you?”

I looked down the hotel bar at the two young women, mid-twenties, clearly out after work. Both pleasingly full-figured, with one a bit on the mousy side, boring blouse buttoned up and holding in what might have been an impressive chest; the other dark hair, a bit more make-up, blouse open enough to invite a man to get caught looking—my questioner. At least 15 years their senior, I had no problem playing it cool and looked her right in the eye and said: “I am six one and 270.”

She maintained eye contact and smiled wryly and said: “You know that’s not what I meant.”

“I know but I thought I would at least tell you my name is Mike and to answer your actual question, more than big enough,” I answered. “But at the risk of being the first person in this conversation to ask a rude question, why do you ask?”

“Well,” she said, playing with the cherry in her old fashioned, “I am trying to convince my friend here that she is making a mistake settling for a man who is, well, lacking.”

The other woman squeaked in protest, “Krista, I have told you Don is just fine and makes me very happy.”

Still holding my eyes, Krista snorted. “’ Just fine’, she says. My friend Nancy is going to settle down with a five-inch, quick squirt loser because she thinks that’s the best she can do. I say she is jumping the gun and has not lived nearly enough to make that decision.”

“Oh fuck,” said Nancy, dejected and embarrassed.

I broke eye contact with Krista and looked at Nancy and said “You know there are plenty of women who are very happy with men with even smaller dicks than that. And you know,” I added, looking back at Krista, “there is something to be said for love.”

“Yeah, yeah,” said Krista “But you aren’t packing 5 inches or less are you? I can just tell.”

“No, I am doing better than that, but I think our conversation has probably reached the end of what we can talk about here. I am going to my room if there is more you want to discuss. 712.” I paid my tab and theirs and went up to my room, fully expecting to watch the rest of the baseball game and go to bed.

I was out of my shoes and tie with my shirt half unbuttoned when there was a knock at the door. I am sure the surprise on my face showed as Krista laughed as she pushed past me into the room. Nancy stood in the hall, a mouse at the entrance to the lion’s den. “Won’t you come in?” I said and stepped out of the way. I followed her and saw Krista was already sitting on the edge of the bed, kicking her shoes off. “Won’t you sit down, Nancy?” I said as I gestured to the armchair in the corner. I walked over to the mini-bar and pulled out a half bottle of overpriced white and opened it…pouring it into two ice water tumblers and handing them to the girls, Nancy first.

As I walked over to Krista, she stood up and walked right up next to me and pulled my mouth down to hers. I was concentrating on a very good kiss when I felt her hand snake across my pants and gently grip my semi-hard dick. She broke the kiss and smiled at me like the proverbial cat with a canary. “I knew it,” she whispered, “I just knew it.”

Then she rounded on Nancy. “First off, he is a very good kisser. Is Don (god I hate that fucking name), is Don a good kisser?” Nancy couldn’t meet Krista’s eyes, let alone mine. She muttered something about Don being a “fine kisser.” Krista snorted. “Don’t lie to me. You have told me he doesn’t kiss much and when he does it’s like he is just waiting to do something else. I have kissed this man, Mike, exactly once and I can tell you he knows what he is doing. When he kisses you, he is kissing you. He is right there, in the kiss with you. Don’t you want a kiss like that?”

Nancy blushed furiously and said, “Yes,” very softly.

I put the wine bottle down and walked over to Nancy. I held out my hand for her to stand up. I looked down at her until she finally looked up and me and I slowly, very slowly, leaned down to kiss her. I was firm but kept the contact soft as I put a hand on her waist. The hint of bourbon from her drink was sweet on my lips and I kept kissing her. She leaned into me and when my other hand touched the side of her face, she moaned into my lips and opened her mouth slightly. I kept kissing her in that position, with my eyes closed for at least a couple of minutes, her body pressing tighter and tighter against mine, Nancy’s hands now reaching up to my face and kissing me back.

I felt Krista move behind and me and while I kept kissing Nancy, Krista started unbuttoning my shirt and pulling it off. Nancy and I had to break our kiss for a while and she kept her eyes closed for a minute and then said “oooooh, wow.”

Krista laughed again and started unbuckling my belt from behind. “Better than Don, sweetie?” Krista asked.

“Oh my god,” was all Nancy could whisper.

How Big Are You? 2

Then her eyes got wide and she looked around…Krista had walked around and turned off the tv and most of the lights while we were kissing. With Krista’s urging, my pants fell to the floor and I stepped out wearing only my boxers, with “my friend” making a good-sized tent in the front. I was worried Nancy would bolt but she just pulled my face back down and I started kissing her again. This time I was unbuttoning her blouse and slowly pulling it off. Then I picked her up and laid her on the bed and she started to look scared again. Krista came over as I stood up and started to take of Nancy’s skirt and sadly boring underwear.

Krista took Nancy’s hand and laid it over my cock and Nancy’s eye’s got very big. “Say no now if you don’t want to do this,” Krista said.

“I…I…want this,” whispered Nancy hoarsely.

I got up between Nancy’s knees and went to slide down to lick her pussy for a while but she put a hand on my shoulder and repeated “I want this!” and she pulled by dick out of my boxers. I stood up, let my boxers drop and heard Krista drop into the chair behind me. I pulled Nancy to the end of the bed and lay by cock head at the top of her pussy. She was already moist to the touch and when I slid my dick up and down along her length I could feel she was positively wet. I put the swollen head of my dick against her and slid the first two inches in and she went from a moan to a full cry: “OoooOOOOOO, OH GOD!” As I slid slowly the rest of the way in, she let out one long steady groan and suddenly her hands were flailing against my chest and her hips were rocking hard on my cock and finally, she tensed up and came all over me. On the first stroke…

Slowly I pulled out and started back in again and her eyes flew open. I smiled and leaned down and kissed her again and again while I stroked my dick into her over and over again. One hand found one of her nipples while the other held me up and she was moaning and using fewer an fewer words as I pumped into her. After another, smaller orgasm, I pulled myself up and started fucking her strongly and steadily in a long, deep stroke. I looked over and Krista had her skirt off and was fluttering her hand across her clit at a high speed watching us. She gave me and evil wink and whether she really had an orgasm right then or was just play-acting for me, I will never know.

I rolled Nancy over onto her side and kept up my pace but from this angle, I could play with both her big sweet tits and her smooth luscious ass. Nancy seemed lost in a haze but Krista got off the chair and kneeled down in front of her. Krista snaked her hand down between Nancy’s legs and leaned in close, an inch from kissing her and said: “Did you know it could be this good?” Nancy gasped and opened her eyes and panted “No…no…no…” I felt Krista’s fingers sliding over Nancy’s clit while I kept fucking her and Krista practically yelled at her friend: “Then come on the fat, fucking dick!” and gave Nancy a huge wet tongue kiss.

Nancy could barely maintain the kiss and started screaming “oh, oh, oh, OHHHH” and came in a huge wave, clamping down on my dick and then just seemed to pass out.

Krista stood up and pulled off her blouse and pulled me off Nancy. She led me to the other side of the bed and pushed me down. “You broke my friend,” she laughed as she started to straddle me. I gave her a big smile as she lowered herself onto my dick and groaned. “And now I know why. Oh, you are exactly what she needed. Thank you so much,” as she pumped up and down on my swollen cock.

I played with Krista’s nipples while she rode me and she seemed to have two or three little orgasms. I told her she was going to make me come and she looked down in my eyes, planted her hands in my chest hair and grabbed hard at me and started grinding her pussy against my pubic hair, harder and harder and then got a beautiful smile on her face as she pulled stream after stream of cum out of my dick.

She rolled off me and slithered down to put my dick head in her mouth. “Mmm wow, that is very good” she moaned and started gently sucking me as I slowly deflated. I swiveled around and started to lick her pussy at the same time and she said “Oh, a real man. Not afraid of a wet messy snatch, are you?” I just kept licking her and started sliding my fingers into her while she went back to teasing my dick. We did this for about 20 minutes, with flooding my hands at least twice and sucking my cock back to hardness.

“Hey, that’s mine,” I heard sleepy Nancy say. She got up and pulled Krista off me and gave her a huge hug. “Thank you,” I heard her whisper in Krista’s ear. Then she pressed herself against me and said: “And thank YOU too.”

She smiled shyly up at me and asked in a sweet, irresistible voice, “Can we do that again?”

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