Dick The Pimp *Swagg Pimpin' 24 7* {The Freaky King of Porn and SeXXX}



Last Updated:

Post New Blog
Manage Blog
Email to a Friend

Gender:
Status: Swinger
Age: 65
Sign: Gemini

Country: United States
Signup Date: September 26, 2019

Who Gives Kudos:


My Subscriptions

11/21/2019 

Mile High with Kathie Lee
Category: Roleplay Stories

I was taking a flight from Los Angeles back home to New York City. It was first class and the service was excellent, very hot stewardesses and they know how to please the passengers. I was napping and dreaming about the two porn chicks I had a threesome with in LA last night.

The first class section was pretty empty. I saw, before my nap, 4 other passengers scattered about, only one old guy about mid sixties range near me.

I started to wake up from my sweet dream when I heard someone sit down beside me, I was in the window seat, and I felt them bump into my left arm as they sat.

I looked over with hazy eyes and shook my head to clear my vision. I saw a sight that made me shake my head again and smile. Kathie Lee Gifford was sitting right next to me.

I've had a huge crush on that woman since the 90's, so I was very pleasantly surprised. She looked at me and smiled. I told her I didn't see her earlier. She explained her seat was on the front aisle, but she felt a little lightheaded, so she sat next to me after she made a bathroom trip. She said she hoped I didn't mind, I assured her I didn't.

She looked so fucking hot. She was wearing a tight white button down blouse that was unbuttoned to right below the top of her cleavage. I could tell she didn't have a bra on and that made me smile.

She was also wearing a short very tight beige mini skirt and the sexiest white designer stripper pumps I had ever seen, and very expensive designer shades. This woman knew how to dress to impress for damn sure.

I noticed when she turned to call for the stewardess that I could see most of her left breast in her blouse. It was a beautiful sight.

Kathie Lee, despite her age, early 60's I believe, still looked gorgeous and her world class breasts were still in damn good shape.

I smiled and quietly took a picture of her beautiful breasts with my phone while she was talking to the stewardess.

The hot ebony stewardess Lolita smiled at me. She knew exactly what I was doing and it turned me on that she knew.

My 7 inch thick cock was rock hard in my thin designer sweat pants and Lolita looked right at it and smiled again. She winked at me, as she went to get Kathie Lee the aspirin she requested.

Kathie Lee looked at me and said, "by the way I never got your name, I'm Kathie Lee Gifford." Looking at her, smiling I said, "I know exactly who you are, my name is Dick, but my female friends call me Big Dick."

I laughed. I was seeing right off how far I could go. She smiled a little but didn't laugh, and said "well DICK, she left out Big as she emphasized my name, it's nice to meet you."

I told her it was a pleasure to meet her. I wondered if I went too far with the Big Dick stuff, but I decided I was gonna march forward and keep pushing the sexual innuendo envelope.

She had her head back resting so I decided to sneak a peak at those amazing tits that I've lusted over forever.

I had my phone camera in my right hand, and a rock hard erection in my pants. I reached out carefully with my left hand and gently moved her blouse out from her body so I could snap a picture of her left tit.

Lolita came back with Kathie Lee's aspirin, but I held my finger to my mouth to signal her to be quiet. She obliged so I winked at her and took a couple of pictures.

I could tell she was enjoying this too. She proved it when she unbuttoned two buttons on her blouse and flashed me. She wasn't wearing a bra, so I snapped a couple of quick pictures of her big tits as well.

Lolita buttoned up quickly, and woke Kathie Lee, to hand her the aspirin.

Kathie Lee took it and thanked her. She sipped the glass of wine she had to wash it down.

Lolita smiled and winked at me. She told us if there was ANYTHING, making sure to emphasize it, that we needed, please make sure to ask and she walked back to her station.

I sat back in the seat, with my phone at my side, and looked at my phone. I made sure Kathie Lee couldn't see the pictures I took.

She sipped away on her wine as I looked forward daydreaming about all the nasty, fun things that I wanted to do to her.

"You know, I've gotten a lot of letters over the years, from male fans, telling me how excited I got them while they watched me on TV." Kathie Lee said as I woke from my daydream.

"They always would say how hard they got looking at my braless breasts jiggling in my tight sweaters and blouses. I just didn't think much of it, although I have to admit I was a little flattered." She said, as my cock got as hard as it could possibly get.

Then she leaned in to me and said "but I never acted on it, so you and your hard cock can get that idea out of your head." She said, deflating my and my cock's excitement, at the moment.

Damn, I thought to myself, as I looked at her, as she started reading a magazine with her co-host Hoda on the cover.

I wasn't discouraged by her little verbal kick in the nuts, so I decided to up the ante on her.

"Well, Ms Gifford, I guess they didn't realize how much of a gorgeous teasing prude you were." I told her. She didn't realize that I don't give up on getting pussy.

She looked at me, with a stern look, taking off her shades as she did. Her face was inches from mine. "I am not a damn prude Dick, and don't ever say that again. I just don't get off on little dick losers trying to talk dirty to me, or take pictures of my boobs while I'm sleeping!!" She blurted out angrily.

I didn't flinch, I'm Dick the mother fucking pimp, so I told her "well lady, your fucking nipples are hard, so I guess you do!" I put her right hand on my rock hard cock and I said, "my cock ain't little and I sure as hell ain't no damn loser!!"

"I thought you were nice, but I guess your co-host Hoda is the nice one." I told her, as she ripped her hand off my cock. "Nice? If u mean by nice that she fucks the interns, then yeah, I guess she's the nice one." Kathie Lee shot back.

I was thinking to myself, damn, why couldn't Hoda be the one next to me then.

"She's always in her dressing room getting fucked or blowing somebody. I can hear everything, my dressing room is next to hers and the walls are thin. I heard her getting ass fucked by the head of the network last week, guess that's how she got the gig on Today." Kathie Lee kept going about her co-host.

"She even told me, during a break one time, that she blowbanged, whatever that is, all the male interns before the show that day. She's a whore." She finished her rant about her supposed good friend Hoda.

I saw my opening. "Well, you are the star of the show and the hottest woman ever on morning TV, so if I had to pick between the two of you, I would pick you to fantasize about." I told her, trying to placate her ego.

She calmed down, at least for the moment, and even gave me a smile. She brushed her finger over her right nipple, through her blouse, as she said "that's very sweet of you Dick, I'm sorry I got so upset and I'm sorry about my rant about that bitch, but she gets all the attention nowadays and I'm the Queen of Morning shows, so it pisses me off." She said calmly.

I told her I understood and I smiled at her. She smiled back, leaning in to me as she whispered in my ear, "you do have a very nice cock, BIG DICK."

That fucking turned me on so damn much. I reached over and squeezed her amazing tits through her blouse. They felt so damn good. They sagged a little but were still so nice.

Kathie Lee moaned softly as I played with her tits. I rubbed her nipples as I groped her C cup tits, pinching her nipples, rolling them between my fingers.

"That feels so good Dick, I love having my breasts played with. You are very good at it too." She said as she started rubbing my cock through my thin pants.

"I lied earlier Dick, when I said it didn't turn me to read those letters from horny fans fantasizing about me. I would play with my pussy while I read them. Sometimes I would stick my favorite vibrator in my ass as I played with my pussy, it felt so good." Kathie Lee said, turning me on like fucking crazy.

She was now jacking my cock, slowly through my pants, as I was molesting her tits roughly. I had unbuttoned her blouse all the way to the last button and had my hands inside of it, on her bare breasts as I groped them. I pinched her nipples hard. I leaned in and licked her neck slowly, softly biting it.

She moaned louder. The old guy nearest us was asleep, so no one could hear us as we made out.

I told her to tell me more about how much of a slut Hoda was. The earlier remarks had me turned on, thinking about her too and I knew Kathie Lee liked telling me how slutty her co-host was.

"Well, what really pisses me off about her is, I have blown a couple of producers in my time for jobs but she has put me to shame. She blows every guy on the show, crew and guests. Everyone assumes Regis fucked me all the time. He did a couple of times, but he has a small cock and he couldn't satisfy me." She said, as she put her hand in my pants and jacked my cock.

"Gellman, the producer, has a bigger cock, but he just wanted anal. After a few times taking it up the ass, I got bored with him and I haven't fucked anyone else on either show I've been on since." She said. I knew she was a freak, oh fuck yeah, I was gonna freak this bitch big time.

I leaned down and sucked her tits, one at a time, pulling the nipples with my teeth, licking them as I sucked them.

Precum was leaking out of my rock hard cock as Kathie Lee worked it so well. She wiped it with her thumb as she jerked my cock.

She put her thumb to her mouth, as I looked up at her, and licked it so seductively, swallowing my precum smiling at me.

"Your precum tastes delicious Dick, I can't wait to taste the real thing. I love cum oozing down my throat. It turns me on to swallow cum." Kathie Lee said, sounding so damn sexy. This woman loved turning me on, that's for sure.

I stuck my hand up her skirt and noticed she didn't have panties on, she had stockings on, but no panties. I rubbed her wet pussy as she moaned, clenching her teeth to avoid making too much noise.

Lolita walked to us and smiled at me again as I started fingering Kathie Lee's pussy. She looked around and unbuttoned her blouse, showing me her beautiful big tits. She then got on her knees and crawled over to me.

Kathie Lee was startled a little, but she knew what was going on, so she went back to jerking my cock while I fingered her wet pussy.

Lolita pulled my pants down below my balls and proceeded to suck my cock. She knew her way around a cock, I realized, as she sucked my whole 7 inches down her throat in one gulp.

I was sucking Kathie Lee's tits hard. I had a whole breast in my mouth as I sucked harder and harder. I then sucked only on her nipple, wanting to see if I could get some milk out of it.

Lolita licked my cock slowly from base to tip as Kathie Lee played with my balls.

I got my wish as a few drops of sweet milk dribbled out of Kathie Lee's nipple. I swallowed them eagerly. She leaned over and started sucking my cockhead as Lolita licked the sides.

I was in heaven, having two gorgeous women sucking and licking my rock hard cock. I just leaned back and enjoyed it, watching them.

I put my hand on the back of Kathie Lee's head as she so expertly sucked my cock. I knew I was gonna cum if she kept it up, but i didn't care. I just wanted to cum in the mouth of one of my biggest crushes.

I felt my cock well up, and Kathie Lee did too. She sucked harder and faster. I couldn't hold out any longer, so I PUSHED up into her mouth and spurted my thick cum into it. Spurt after thick spurt of cum filled her mouth, and she swallowed it all eagerly. The sight turned me on so fucking much.

She lifter her head up, turned to me, opened her mouth and showed me the rest of my cum she had in her mouth and swallowed. She licked her lips and told me it was delicious.

Lolita smiled at me and stuck her long tongue out, licking my cock head, getting any drops left over. She swallowed what was left and sucked my cock clean.

I told Kathie Lee I just had to cum in her mouth, but that I was ready to go again and again. My hard cock proved it.

She smiled and said "meet me in the bathroom baby. I wanna get fucked in the ass while I watch us in the mirror."

I said "Yes ma'am" and looked at Lolita, winking at her.

Kathie Lee went to the bathroom, making sure no one saw her with her blouse almost off.

I got ready to join her as Lolita got up and went to the aisle. I looked over and saw the old guy was waking up.

Lolita winked and went over to talk to him as I went to the bathroom to fuck Kathie Lee's sweet ass.

I knocked on the door and Kathie Lee opened it. She pulled me in and locked it.

I kissed her, squeezing those beautiful tits, then I spun her around to face the mirror. She stuck out her tongue with a devilish grin on those ruby red lipsticked lips.

I was so hard, my cock felt like a bar of steel. I ripped open her blouse all the way, popping off the last button. I pulled up her tight mini skirt and pulled my pants down.

I pulled her hair back hard as I gripped my cock, looking at her in the mirror. I said "ok bitch, u love getting ass fucked so much I'm gonna tear your ass up."

She smiled and told me "make me your bitch baby. I'll do anything u want, use me, degrade me, anything baby. Fuck my ass hard, it's all yours from now on."

Smiling big, I shoved my bar of steel cock all the fucking way up her slut ass. I pulled her hair as I used her ass, drilling all the way up her sexy ass every stroke.

I smacked her ass as I pounded it, in and out. My cock, and me, loving every fucking second in that famous ass.

"YES BABY YES, TAKE ME, USE ME, I LOVE YOUR BIG FUCKING COCK IN MY ASS YESSSSS!!" Kathie Lee shouted. I knew I had her hooked, so I kept up the hard pounding of her ass.

I smacked her ass again as I reached up with my left hand and squeezed her tit so hard, pounding the shit, no pun intended, out of her ass hard and fast.

She was moaning loud and squirming, loving my thick 7 inches up her slutty ass. "Fuck yeah baby, it feels so damn good, I love ur Big Dick, Dick. I'm yours, I'm your bitch now baby." Kathie Lee shouted.

I was fucking her ass so hard, the small counter she was leaning on, started shaking. I drilled up her ass a few more strokes, then I came up her ass. My warm cum filled her ass. She moaned and sighed as she smiled, my cock still cumming in her ass.

After I finished cumming in her ass I told her to sit on the toilet. I was gonna test her loyalty to me. She sat down looking so fucking sexy. I pointed my half hard cock at her mouth, it was open, so she knew what I wanted, and I pissed right into the famous mouth of Kathie Lee Gifford.

I pissed a mouthful and she swallowed, without me telling her to, and I pissed another mouthful that she once again swallowed. I pissed five mouthfuls of piss in her mouth that she swallowed and I shoved my cock down her throat for the last load of piss. I could feel it going down her throat, she didn't even gag.

"Damn that was fun Kathie Lee, your right, you are my bitch now. We are gonna have so much fucking fun." I told her, then we fixed our clothes and went back to our seats.

We sat down and as Kathie Lee was fixing her lipstick, I looked over at the old guy and saw Lolita sitting in his lap. She was facing away from him riding his cock.

I told Kathie Lee to look over there as Lolita turned her head towards us. She looked at them fucking and put her lipstick down, rubbing her nipples.

I started playing with her tits from behind as we watched Lolita ride the old, fat businessman.

Lolita then turned her right leg towards the seat, her miniskirt bunched up around her waist, showing us that he was fucking her black ass.

Kathie Lee's nipples were rock hard as I played with her tits watching the fucking across the aisle. I was kissing her neck as I fondled her tits. Lolita blew me a kiss as she rode the old guy, taking his small cock in her ass.

I could see the expression on the old guys face as he came in Lolita's sexy black ass. She got up after he finished, fixed her skirt and smiled at him, then she made her way over to us.

I stopped playing with Kathie Lee's tits as Lolita came over to say, "I felt sorry for him. He was lonely and I was still horny so I decided to help him out."

I told her, with a sly smile on my face, that they have excellent service on this airline.

Lolita then got on her knees and crawled over to me, taking my cock out and sucking me so good. I looked over at the old guy and noticed he hadn't put his cock back in his pants.

I saw Kathie Lee looking over at him too, as I rubbed her nipples.

Lolita was now fucking my cock with her big tits, they felt so good. I looked at Kathie Lee, as I smiled, then nodded towards the old guy. She got my meaning, smiling her devilish smile at me and walked over to him. She got on her knees in front of him, startling him, and she started sucking him clean.

I was fucking Lolita's big black tits as I watched Kathie Lee suck the old guy's cock.

I was so turned on I didn't last long. I looked at Lolita as she sucked the head of my cock and I came so hard in her mouth. I looked over at Kathie Lee as she finished licking the old guy's cock clean. She got up and walked back towards me.

Lolita swallowed every drop of cum I shot in her sexy mouth. She sucked and sucked and sucked as I came.

Kathie Lee sat down beside me and started stroking my cock, as Lolita sucked it.

Lolita opened her mouth and showed me the last mouthful of cum I had just put there.

Kathie Lee leaned down and kissed her, as they cum swapped my thick cum. They showed me, as they played with it, with their tongues.

I laid back in my seat smiling, looking at the two gorgeous women that just rocked my flight. I fucking love getting all freaky on a flight. The mile high club is definitely at the top of my cool clubs list.

The pilot came on the intercom and said for everyone to prepare for landing and welcomed us to New York City.

When we landed Kathie Lee hugged me and told me she had the best time sexually she ever has.

I told her she was one sexy bitch. She looked at me with that devilish smile and said "Yes i am, your sexy bitch." I smiled a big ass smile and kissed her.

She told me she wanted me to move in with her, so I did. We have been fucking our brains out day and night. True to her word, she does whatever I want. She even invited Hoda over for a threesome. I got to try out her ass and piss in both their mouths also.

Kathie Lee knows how to keep me happy and so very happy I am.

10: PM 0 Comments  (Add Comment)  |  

Back to Blog List

Back to Blog List