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First date Stories

first date

Oh, What Beauty!

The first time I saw her and the time that's passed...

Oh, what beauty did I spy The first time that you caught my eye. Lips so full, tender and sweet, Eyes to steal my soul complete.   Oh, what beauty, I am taken aback By hair so long and silky black. Angels wings and heaven's bliss That heat filled moment, our first kiss.   Oh, what beauty do I know? Our first date down, a million to go, Weeks to months and every day You stay with me, is what I pray.   Oh, my beauty, you we...

Winter is Cumming part 2

I take my new gf on a day of shopping, burgers and aging hair bands

As the bright, invasive afternoon sunlight came streaming through my stained (with dust and dirt) glass window, I found myself spooning (and possibly forking) with my new dream girl, Winter Summer, whom I had met earlier at the Public Market. Rubbing my aching jaw from our earlier sexcapades, fearing I might have lockjaw then grinning like an escaped lunatic as I recalled her hairy pussy, suddenly so afraid she might be a...

Frightful Weather is Delightful

A first date evolves as the weather turns

The evening wasn't going as planned, but that was a good thing. It was supposed to just be drinks after work but it had turned into dinner and now they were still lingering in the restaurant hours later. David looked around the little steakhouse. The couple at the last remaining table was putting on their coats. He sighed. "This has been so much fun but I guess we're going to have to call it a night," he said, returning h...

A Date Gone Wrong, Chapter 1

He seemed like a nice enough guy... what could go wrong?

It was just supposed to be a simple ordinary date. Nothing that Maria hadn't done many times before. But this particular date would change the course of her life forever. She had met him at the club a few nights ago when she and her B.F.F. Jenny went there for a "girl's night out" after a long day at work. Both girls had a bit too much to drink that night and Jenny got sick in the ladies room, but in whole, it was a fun t...

A Night Of Firsts

Helping a divorcee discover her sexuality

The date did not get off to a good start. I arrived early as always, ordered a drink and found a nice seat outside to enjoy the amazing summer sun that for once was beating down on London. As the minutes ticked by I began to think that I’d been stood up. Suddenly, fifteen minutes late, my phone buzzed with a message apologising but assuring me she was on her way. She finally arrived thirty minutes late and I was taken aba...

At fourteen, I was far too young for my mom's twenty-one year old server. Jake and I knew this, and agreed friends was all that we were allowed to be for the time. The friendship would end though, and we would lose touch.Why did it end? Scribbling my name with his last name on my notebook was cute, until mom found out. Just like that, my mom left her job to go to a new company, and deleted his number from my phone and tol...

Longest Date

There I sat, on top of the worktop of his kitchen island waiting in anticipation..

There I sat, on top of the worktop of his kitchen island waiting in anticipation and wondering how I ended up in there. When I first saw him I never thought I would end up here. Bra-less in the kitchen of a man I barely know.Two days before we had our first date due to my friend. It seemed that she had made it her mission to bring us together and like two teenagers we fell in her trap. For weeks he passed my desk at work,...

Movie date leads to more

Charlie and Mandy start to discover themselves on a movie date.

Charlie and Mandy were in the same class in college. Charlie always had a thing for Mandy right from the first time he had laid his eyes upon her. Even though Mandy initially played hard-to-get, gradually Charlie was able to woo her and she agreed to go out with him for a movie.So, they went to the theatre and got the tickets for the newly released romantic comedy. About fifteen minutes into the movie, Mandy was feeling b...

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The Next Day

The day after the first date, her fragrance remains and keeps him wondering

It is over a day since I said goodbye. Twenty-six hours to be precise.For all of her talk about fragrance sensitivity, it is now me talking about scent.I can still smell her on me. I know that can't be happening. I showered this morning, washing off the remains of yesterday. Washing off the touch, the embrace, the kisses. Washing off the outward connections made over the course of a day. I know it can't be happening.Yet I...

I was a senior in high school at the time. Even twenty seven years later, I can remember everything about that Friday night. Well, everything except the movie. It was June, 1988 and I had just asked my long term crush out on a date. I couldn’t believe it when she accepted my offer to go to the cinema that Friday. Becky Waters was the most popular girl in school and I was pretty much not her type, she usually went for big,...

Sex At The Cinema

It was their first date, and they didn't care about the movie!

It was our first date. I had met Aubrey in the library a couple weeks ago both reaching for the same book. We talked for a few moments and realized we had a lot of similar interests. We exchanged phone numbers and began texting one another. Texting gave way to flirty sexting and soon I wanted to actually go out with her. So in one of our textings I asked Aubrey if she would be up for it and she said she would love to go o...

The Little Black Dress

Meeting a woman for dinner and the outcome is explosive

“I need your opinion on a dress I have just bought if that’s okay,” you ask casually. “Of course,” I reply. You disappear off upstairs, leaving me sitting in the lounge feeling somewhat bemused. I’ve enjoyed such a delightful meal, with a beautiful woman whom I haven’t seen for years. I am now feeling somewhat on edge, by your request for my viewpoint on a dress! Candles flicker in the fireplace as I nervously perch on th...

A Date For The Weekend Chapter 1

A perfect date for the weekend leads to more.

I've been crossdressing and living as a woman full time for years. I put a lot of time and work into transforming myself into an attractive woman that can accompany a man anywhere in public and never raise an eyebrow. I've long since moved on from having casual cheap hookups to expecting more elaborate playtimes, and generally only date men if we can plan a weekend or more together. I mean, if I spend all this time and ef...

Beautiful Mess - First Date

Captain Jack and Julie's First Date

The morning is a whirlwind of getting my things thrown together and back home, so I can shower and change for work. I had no intentions of sleeping at Jack's last night, but after the mind-blowing sex we had, how could I not? It was after all, a beautiful mess. As much as I thought I would fight my feelings with Jack, everything seems so right, the way he makes me feel safe, like I can trust him, how we interact with one...

His Hands

Our first date became something more very quickly.

His hands were large and soft. That was always the one thing I remembered most about him. When we would lie together he would run his hands up and down my torso. Caressing me gently, warming me all over slowly. In those moments I would sigh and snuggle closer to his hard body. Yet now when I turn over he is not there, just a cold empty bed to caress and comfort me now. My Trent is gone away. I huff and turn over, imaginin...