First Date Stories

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Practice Date with Kim

by ScottArroy on Sep 14, 2020
Romance

Copyright ScottArroy August 01, 2020 https://www.literotica.com/s/practice-date-with-kim This was my first story written on Literotica. It has been revised for improved reading. My sister asked me to help out her best friend. Now I have known Kim since she went to kindergarten. She is intelligent, kind and sexy and if she wasn't my sisters bestie she woul...

Michelle's New Profession Ch. 03

by robertl on Sep 26, 2017
Loving Wives

This story follows directly after Jacqui's Wedding, Chapter 2. Thank you very much to Shygirlwhore for editing assistance. ***** Monday after I got home from work, Michelle and I had fun going through her escort service e-mails. If they had the words 'fuck', 'cock', or anything comparably crude in the subject line we deleted them. Michelle loves romance. S...

Not Scuba Diving Ch. 02

by tanglosax on Jan 8, 2019
Loving Wives

Thanks for all the comments, positive as well as negative, on my first attempt. Look forward to more comments on this effort. I did not title the first story as Ch 1, but you should read it to make better sense of this ch. 2. ***** Late Tuesday night Julie and I arrived home after I rescued her from her initial attempt to go on a date -- a date with anoth...

Formal Dinner Delights

by kandie on Sep 1, 2017
Group Sex

As they take their seats at the candlelit table, he can see that she is dressed for the occasion. Her simple black skirt is short enough to show her black nylon stocking tops. Her low cut blouse lets him see her very lovely breasts almost to the nipples. The waiter arrives to take their order. She looked at him and was surprised, here was this tall muscular...

High Society

by MungoParkIII on Sep 17, 2017
Text With Audio

* * * * * Click Here to listen. (4.5 min/mp3) * * * * * She was always so prim and proper and though never one to unduly criticize she'd turn her head in shock when others talked of the way some slut came on to a boyfriend or brother of theirs. With her you had to have manners and you were expected to actually take her out on dates if you wanted to spend...

Sparkling Red's Story No. 03

by SparklingRedRules on May 11, 2020
Romance

Sparkling Red's Story No 3 - Jardine Man and our First Date - naked! Jardine Man 'likes' me on Zoosk, shortly thereafter he sees his opportunity and, after a few Personal Messages, he asks me out for a date which is set for midday at the Wharf Restaurant. I like his choice as it's the best restaurant in town or at least I think so. He has indeed come on hi...

Men's Sexual Confessions: Charlie

by PositiveThinker on Aug 30, 2017
Erotic Couplings

Best Buddy's Sexual Peccadillo Group of men sit around talking candidly about their sex lives. I'm Paul, the host of this party. Thanks for stopping by to read my story. We were all sitting around the big screen watching the Super Bowl one year. I had invited all of my best buddies to watch the game with me. There were 21 of us guys, including me. Our wiv...

How I Learned to Date as a Girl

by TammyPanty on Jan 7, 2018
Transsexuals & Crossdressers

Learning how to date as a girl By the time I was 25 years old I had really perfected my female look and practiced acting and thinking like a girl. I was very confident in my look and actions. I had been out in public many, many times dressed as a girl and I blended in perfectly. With this type of confidence I decided to take the next step and see if I could...

99 First Dates Ch. 02

by Stultus on Sep 14, 2017
Humor & Satire

The litany of romantic horror continues... 18. Ms. Stuck-Up Bitch - I've had first dates where the woman was rude or snide or otherwise disagreeable, but never to the extent that this woman demonstrated. If she had anything nice or pleasant to say during our brief coffee date than I must have blinked and missed hearing it. She made especially rude comments...

Fucked on first date

by Dumbpotatoes on Apr 22, 2025

Julie was in her apartment getting dressed for her first date. She wore rather conservative clothing, buttoned up shirt, nice shoes, dark tight fitting jeans, and of course underwear (bra included). Just as she was about to leave, her roommate Melanie walked in. "Ah, I caught you. Just in time." Melanie sounded relieved. "Not really, I have to...

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