“Do you want to cum in my mouth?” A Memoir
“Do you want to cum in my mouth?” As soon as she said that, my heart skipped a beat and my fucking lost a few strokes. It was so mater of fact, like “Do you want cream in your coffee, Sir?” It was the first time a woman had asked me that question, and I had had lots of partners in many sexual settings over the years before.
Chicago… 30 Years Ago… A Memoir
It was winter, and typical Chicago weather… cold and snowy. I was in charge of the bar at a nice restaurant in the shadow of the Sears Tower, just west of the Loop. We were one of the sponsors for the yearly production of A Christmas Carol at the famed Goodman Theater, and offered a package Olde Fashioned English Feast in the Dickens tradition with transportation to the theater and back for ticket holders. The final performance was on New Years Eve and the restaurant was hosting a party for the staff and backstage crew of the theater after the show.
The turnout was pretty good… who doesn’t like free food and drink. One of the guests was alone and hung out at the bar talking to friends, and as the partygoers left for other parties or home, she was talking to me. Not flirting, just talking as she seemed lonely, and I was enjoying the attention of a pretty girl half my age. I found out she was a lighting technician and was now out of a job, so the closing was bittersweet, as she was not needed for the next show. Beth was an attractive woman in her early twenties with a full figure, but seemed ill at ease in her dress, like she was not used to dressing up, and certainly wearing heels. As the party wound down and I gave last call, she asked me if I would dance with her… that was how she put it…. and I told her I would love that. By that time of night, the music was slow and dreamy and she put her arms around my neck and melted against me. I was just there to dance, but could not stop the stirring in my pants and I knew she could feel me stiffening against her. We didn’t talk or get romantic, but it felt good to hold and feel each other. We danced the last dance and went back to the bar. I started to clean up the bar and she hung around watching. I was deciding what my move should be, when she asked me if I wanted a ride, since it was “snowing and you have to take the train home”, she said. She had made the move, and I appreciated the ride.
Her car was an old yellow Datsun, named Woodstock. I don’t know why women like to name their cars, but my second wife’s baby-blue VW Beatle was named Wolfgang. I hate driving in the snow, but she was good at it and we got to my place safely. Of course I asked her in and soon we were on the couch kissing and getting naked. I always liked to leave a woman’s bra and panties on and suck and kiss through the material before removing, which I thought was sexy and hadn’t had complaints so I guess they thought so too. Beth had small conical shaped breasts with long nipples which I sucked and nibbled as she stroked my cock, letting go as I slid down her body to kiss around the top of her mound and stroke her inner thighs, circling closer to her panties. Soon kissing and sucking, drawing the silken fabric into my mouth. I am tempted to say I ripped them off with my teeth, but I didn’t and gently slid them down her legs with one hand as I palmed her mound with my other, thumbing the hairy slit. She was pretty silent and I hoped she was enjoying the sex, as I kissed and parted her lips with my tongue, sucking her clit into my mouth. I felt her hand on the back of my head as she began to thrust her hips up toward me. Her eyes were closed and I could see her fingers squeezing one of her nipples. I wanted to try to give her an orgasm but I also wanted to fuck her and my cock was winning out, as I moved up and rubbed the head of my dick up and around the entrance to her well lubed slit. God, I was moaning and she was still silent, breathing between her teeth as I pushed inside her. After a few strokes, like an idiot, I asked her if she liked it and she dug her nails in my back. Beth’s full ass felt good in my hands as I squeezed and drove my cock slowly in and out of her pussy. I rose up so my shaft was rubbing against her clit before pushing back up inside. I asked her if she liked to be fucked from behind, she said yes but not to stop what I was doing. Thinking I was going to make her cum was having an effect on me and I imagine she could sense it, because out of the blue she said, “Do you want to cum in my mouth”. Now, that blew me away, quite literally as I plunged deeper and faster saying “Yes!”. Soon, I rose up and she grabbed my cock pulling me toward her. I made it as far as her chest covering her neck with my jizz. She drew the head into her mouth and sucked me softly. Beth stayed the night for sleep and more sex.
We got together a few more times to have dinner or go drinking and have sex, until one night she came into my neighborhood bar and introduced me to her boyfriend. Now that was a surprise. She said she might be going back to college, we lost touch and I never saw her again. But, I will never forget her and the night she asked me if I wanted to cum in her mouth.
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Author’s note… I was never an ‘I want to cum in your mouth’ kind of guy. During a blowjob sure, but I wasn’t going to go out of my way to do it when we were fucking. My first wife wanted to try it and she liked it okay. My second wife hated it. And, the one I should have married absolutely loved to suck cock and get a mouthful of jizz, the funny thing, she did not like to have her pussy eaten, which was disappointing, because that’s one of my favorite parts of sex. The memoir above is a true story as it happened. I often think of Beth and wonder if she ever pursued a career in the theater… I sure hope so.
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I figured all Rebel’s Wicked Friends might like this story and wonder how many have asked that question. Of course it applies to men as well as women, for I have asked many a woman to cum in my mouth.
p.s. sorry, no chocolate in this story… but, as I recall, there were some bowls of Hershey Kisses at the party… does that count, Marie?
23 comments on ““Do you want to cum in my mouth?” A Memoir”
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Life of Elliott... 
Oh chocolate?! Yeah …
So into your memoir I forgot about the chocolate prompt lol
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Such a lovely memory to share. I have never asked a man if he wants to come in my mouth. It took me just more than 40 years to allow a man to do so anyway…
Rebel xox
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It is such a sexy question in my opinion
Mollyxxx
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Oh my. 😶 what a very nice memory. I’ve asked that question before…
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It is such a turn on for a man to hear that. The other thing that will get me going is when a woman says that she shaved or waxed before the date. I’ll beg to give her cunnilingus then.
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Now I know why you like chicago so much
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