I go on first dates with pigtails in my hair.

Cute Glasses Guy hit on me at the masquerade ball Friday night. When was the last time that happened?? He insisted I be in his photo booth picture and stood tall behind me with his arms wrapped around me.

He disappeared and I saw him taking pictures of the other masked guests and forgot about him as I drank three gin and tonics and tried valiantly not to appear chilled to the bone.

Later, he found me on the front porch of the house minutes before my girlfriend and I gingerly managed the the steps in out high heels to The Neighbor’s chariot. I said I had to go, but let him squeeze a breast and get my number. I had another party to attend.

He texted me several times in the car before I noticed TN had surprised me by dressing up in masquerade, too. He was going to join us.

Sitting next to my young lover and texting a stranger anonymously was like drifting in outter space. I was weightless and irresponsible.

Cute Glasses Guy wanted to know how to grab my breast again. I told him to buy me dinner; the alcohol made me bold. But when he asked me out last night, I said no. I’d spent the night with TN and all day in his bed and on his cock. I needed to be alone.

But, here I am now at a local wine joint with CCG. I haven’t gone out with a man from real life in over a decade. I don’t know how old this man is, what he does, his “voice,” nothing. I feel deaf and blind. Fuck, he doesn’t even know what I look like, which is why I told him my hair would be in pigtails.

Gotta go. He’s here now.

A 40-something single mother who writes honestly about sex, body image, D/s, relationships, her nervous tics, and how much she loves to fucking fuck. She also likes to show you her tits.

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16 thoughts on “I go on first dates with pigtails in my hair.
  1. Oh Dissolute One … you are seeking immediate answers. Why the rush? Start enjoying the journey, and all your answers will come in due course.

    Above all, relax, stop thinking, and have some fun!

    xo Mike

  2. Good luck!
    By the way, “But when he asked me out last night, I said no. I’d spent the night with TN and all day in his bed and on his cock. I needed to be alone.”
    That is the best line I’ve read all day!

  3. Damn, I gave it some time so I could come back to some hot update….sorry it sucked. I think things are shifting in the way that most normal (relative term of course) people aren’t afraid to go online to find a date/match/soulmate/friend. Real life meeting like in a bar doesn’t seem as safe as meeting a random stranger online that you get to know bit before meeting, by exchange texts/pics, etc. Of course being introduced by friends seems best still….anyway sorry he turned out to be a dud because it sounded like it could have been really fun.

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