Younger Guys Dating Cougars

Discussion in 'The Howard Stern Show' started by Streetfighter, Sep 1, 2014.

  1. Streetfighter

    Streetfighter Well-Known Member

    Reputations:
    1,520
    Joined:
    Jan 8, 2014
    Messages:
    208
    Likes Received:
    460
    Howard related because he runs those "Cougar Life" spots!


    I'm 22, and she's 41. We'll call her "Opal". Opal and I met online about a year ago now. We talked for several months before we met in person. We had a lot in common, both tired of our recent relationships and we just wanted something that wasn't so serious. Then we found out that we actually had a lot of interests. It was weird being so interested in a woman who was nearly twice my age, but I never wanted to stop talking to her. Oh...and an important fact to this, we were both very open about our BDSM sides. She's more dominant, and I'm a switch.

    Eventually we met up, but we both had the same thing in mind. However we couldn't go anywhere...I had a roommate who was always home and her mother lived with her. She said she had a pick up truck and we could go to the drive-in or something.

    I met up with her at the parking lot of the mall, got in her truck and we both just smiled after I got in. I put up the arm rest and leaned in to kiss her. She didn't hesitate to kiss back, not one bit. We kissed for a few moments, stopped, looked at each other and laughed. She said that she was hoping I'd be eager to kiss her, and she was more than correct on that point. We drove around for a bit and decided to not go to the drive-in theater. We just drove around for a bit, talked, and then found park. Rolled down the windows, let the nice breeze roll in and talked more. After about an hour of being in her truck we started talking about how we didn't expect this day to go like this. She flat out told me she had the money to get a hotel, but after talking for just the first 10 minutes she didn't want to do that, she wanted to get to know me. I was entirely okay with that, actually I felt better that she said that because I felt the same way...and had my credit card on me just in case we did get a hotel.

    We started making out and she grabbed my groin. She said "I'll need to fix that" and reached down my pants, and started playing with it. I felt incredibly nervous because we were practically in public. My heart racing, but the excitement was too good to resist. I stripped my pants and boxers and she started going down on me. After a few minutes she came up and said "make it rough for me" and I didn't take a moment, I pushed her head down, thrusting myself down her throat. Hearing her gag was such a turn on, and she told me before she loved doing that when she's in the mood. I kept going and going, I never had a girl do this before...a girl who let me be this rough for a blow job. I told her I was about to cum, clearly said it to her, but she kept going. I thought "fuck I hope she heard me"...I came so hard in her mouth. She came back up and kissed me. Tongue down my throat and I was tasting myself for the first time...ever. The rush was amazing, it was mind blowing.

    It was over whelming, but in a great way. I had to take a moment to breathe and she just laughed at me. She said "I hope you were okay with me doing that, I thought you might like the surprise". I said " 'Opal' I've never even thought of doing that, but I absolutely loved it". She giggled and grabbed a towel (seriously this girl was prepared) and cleaned my "down there" area up.

    I couldn't wait to see her again. It sucked being an hour and 20 minutes away from each other and working 40+ hours a week. We met one more time before having sex, and it was the same sort of thing. Before we had sex though she said she sees me more of a submissive guy to her, and I was all for that. We kept trying to meet, but our work schedules were so out of whack it took months. On top of that her mother lived with her and her mom was in a wheelchair, so it wasn't like she was out all the time.

    "Opal" called me after not talking for a couple weeks and told me she needed to see me. Some pretty messed up things had happened in her life and she was stressed. We had a heart to heart about it, and I went there as soon as I could. She even took a day off of work for me to come see her. I went there without sex even being on my mind, I just wanted to be there for her as a friend. She was beyond stressed, and what she really needed was a vacation.

    I got there around 10AM on a Tuesday. I walked into her house, and she hugged me so tight. She was like glue to me, and I didn't want to let go. She whispered "I'm so glad you're here" as she let go then lead me to the living room. We sat on the couch together and I held her as we talked. Things got a bit emotional, she's been through an indescribable amount of shit lately. I'm there for her and after a few minutes she calms down, thanks me for coming again and again. Then we just sat and watched TV for a bit. She got up and faced me, crawled onto me and lifted up my shirt and started kissing my stomach. I instantly got hard, and she knew it. She quickly stripped my shorts and boxers and began giving me head. After only a few seconds, she got up took her shirt off, didn't have a bra on, then took her pants off, and no panties on and bent over. She looked back and said "eat me...boy". I didn't take a second to waste, I got on my knees and started eating her out. Her taste was different, not as intense, and I just wanted it more. I kept going, getting rougher, and shoving my face into her more. Her moans made me fill with passion, the way she would push back on me. Feeling her soft skin on my face and cheeks. I just wanted more and more. I asked her if she could just sit down and spread her legs. She did so and the feeling of her soft legs on my shoulders, her thighs glazing against my face. The feeling of her hands on my head, pushing lightly at first and gradually pushing harder. She cracked a joke "sure you can breathe, I don't want my boy to have any trouble?" I looked up and said "push harder Mistress" and she gave me this smirk I'll never forget. She held my head down, and moaned louder. The twitches in her legs made me think she was going to cum soon. I was right, but another surprise...she was a squirter. She stopped pushing my face and fingered her self viciously. She squirt all over, on my chest, the couch and floor.

    She didn't say anything, just stood there breathing heavily and with this small smile on her face. I stood there with a hard cock, and a wet chest with her fluid slowly going down my stomach. She finally looked at me and told me to get on all fours.

    I'll type more later, I have to get going.
     
  2. mape

    mape Well-Known Member

    Reputations:
    21,720
    Joined:
    Jul 2, 2012
    Messages:
    2,537
    Likes Received:
    4,731
    What the fuck? U writing a book. U have to post us a pic if we are going to get so involved and read all that....Geeezz!:coffee:
     
  3. ice cream

    ice cream Well-Known Member

    Reputations:
    17,105
    Joined:
    Dec 22, 2011
    Messages:
    22,995
    Likes Received:
    4,686
    fuk off gary
     
    Wesmantooth, reno, Ben Dover and 5 others like this.
  4. The Snork

    The Snork Well-Known Member VIP Gold

    Reputations:
    2,418
    Joined:
    Nov 3, 2012
    Messages:
    5,545
    Likes Received:
    8,600
    Dear Penthouse,

    I never thought this would happen to me.
     
  5. Patron

    Patron Well-Known Member

    Reputations:
    8,310
    Joined:
    Feb 28, 2012
    Messages:
    2,092
    Likes Received:
    1,704
    Whoa!...I'm definitely not reading all that
     
    Jayla and Mazley like this.
  6. Stargrave

    Stargrave Active Member Banned User

    Reputations:
    -1,726
    Joined:
    Aug 27, 2014
    Messages:
    164
    Likes Received:
    133
    What a load of bullshit.
     
    reno, smichal, Jayla and 2 others like this.
  7. Mr Fantastic

    Mr Fantastic Found Nemo VIP

    Reputations:
    116,015
    Joined:
    Oct 21, 2010
    Messages:
    9,086
    Likes Received:
    22,485
  8. Mazley

    Mazley Black Knight Banned User

    Reputations:
    -34,811
    Joined:
    Jun 23, 2013
    Messages:
    8,158
    Likes Received:
    4,666
  9. Lola

    Lola little-known member

    Reputations:
    35,280
    Joined:
    Aug 27, 2010
    Messages:
    1,149
    Likes Received:
    1,614
    who is this clown? [​IMG]
     
    reno, Sammy13, babybear and 4 others like this.
  10. Blur

    Blur Alumnus

    Reputations:
    74,772
    Joined:
    Feb 1, 2014
    Messages:
    6,434
    Likes Received:
    9,574
    Totally this.
     
    Jayla and Mazley like this.
  11. BethsZygote

    BethsZygote In Utero VIP

    Reputations:
    3,561
    Joined:
    Feb 28, 2012
    Messages:
    5,609
    Likes Received:
    733
    i actually did read all of that.


    Who the fuck cares?
    and btw, no one believes you, and your story is shitty.
     
    smichal and Jayla like this.
  12. fixer

    fixer I'm Retarded you Jerk. On the Power.

    Reputations:
    372
    Joined:
    Jan 16, 2014
    Messages:
    1,219
    Likes Received:
    2,116
    After the words eat me boy, did you open your eyes and noticed a big cock looking you right in the face. K.C., I knew it was you.
     
    Lola and smichal like this.
  13. AGT Blows

    AGT Blows Well-Known Member

    Reputations:
    79,083
    Joined:
    Dec 30, 2011
    Messages:
    10,616
    Likes Received:
    6,070
    tl/dnr
    Seems like a bunch of me, me, me fake bullshit.
     
    smichal and Jayla like this.
  14. pickles3000

    pickles3000 Well-Known Member Banned User

    Reputations:
    31,090
    Joined:
    Aug 11, 2012
    Messages:
    1,517
    Likes Received:
    4,700
    [​IMG]
     
    Ctanner and Petal like this.
  15. Quite Frankly

    Quite Frankly Well-Known Member

    Reputations:
    9,282
    Joined:
    Nov 19, 2012
    Messages:
    3,986
    Likes Received:
    2,262
    [​IMG]
     
    RenchFries, smichal and AGT Blows like this.
  16. pfchongs

    pfchongs Active Member

    Reputations:
    -342
    Joined:
    Jan 17, 2013
    Messages:
    180
    Likes Received:
    53
    Tl;dr. Op is a faggot
     
  17. Sickboy

    Sickboy Latverian Monarch

    Reputations:
    48,234
    Joined:
    Jan 18, 2012
    Messages:
    4,196
    Likes Received:
    6,464
    [​IMG]
     
  18. peterfonda

    peterfonda Well-Known Member

    Reputations:
    9,996
    Joined:
    Dec 2, 2012
    Messages:
    6,697
    Likes Received:
    5,417
    Did you copy this out of Literotica?
     
  19. chuk

    chuk Well-Known Member

    Reputations:
    130,781
    Joined:
    Mar 1, 2012
    Messages:
    13,718
    Likes Received:
    7,586
    You both sound like real winners.
     
    Mantis likes this.
  20. Brokenbad

    Brokenbad Well-Known Member

    Reputations:
    23,294
    Joined:
    Apr 23, 2012
    Messages:
    5,097
    Likes Received:
    4,368
    Was it real squirt juice or piss?
    Did it taste good?
    Are the floors carpeted?
    [​IMG]
     
    RenchFries likes this.