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The First Date

IntroTo start, just a little bit about myself. I am a 34-year-old crossdresser that has been dressing for most of her life and has reached a certain breaking point of needing to transition. My stories are a way for me to deal with my dysphoria and provide me with guidance as I continue this journey. I’ve met folks that have inspired me to write these stories, so, for now, they are a work of fiction, but maybe one day a reality.Chapter 1We had been chatting back for forth for weeks, Sir, as I...

Plus sized Blind Date

Being a good-looking jock in college was a good thing for Zack Reynolds. His male peers envied him because of his easy-going natural charm that drew girls to him like moths to a flame. But eventually Zack was drawn into a steady relationship with Jill, the head cheerleader. She was sexually adventurous and so physically enthusiastic that she often wore Zack out in bed. After they had been in an exclusive relationship for 3 months, Jill asked him for a favor one night at the dinner table at her...

An Ordinary Movie Date

His car came to a stop in front of the house making that horrid rattling sound that it did. Before he could even turn the ignition to kill the beast, she came walking out of the house with a skip in her step. Lucas watched eyes agape as his new girlfriend Kristina made her way to his car. She was so beautiful, way out of his league and he knew it. “Hey babe,” She stuck her head through the driver side window and gave him a kiss. “What took you so long? I thought we were gunna miss the movie for...

blind date

Hello to all,I've always been a shy person and never been on a blind date till now.One of my friends had set me up with one of her friends as a blind date her name was Jane and I was to meet her at the club down the road.The shyness kicked in I didn't know what to expect but I went along with it anyway.I was sitting in the bar nervously looking for her when my phone rang it was a message from Jane wondering where I was so I sent a message back saying I was at the bar.When I looked up from my...

Dinner Date

I have a friend and her name is Brittany. She's 28 years old, about 5'4 and around 135lbs. She has black as night hair and a beautiful set of perky tits as I would soon find out. Brittany has been a very good friend of mine ever since she dated my brother about 10 years ago. They broke up but Brittany and I stayed close over the years. I never really viewed her as a sexual partner, even though she is incredibly beautiful. We would hang out by ourselves quite a lot. Going to movies, dinner,...

My first date

So last night I took out a man on a date for my first time. It was someone who I already knew. I hadn't seen him in quite awhile. He was the best leather sex that I had ever had. We had kind of lost touch and I wanted this to change. It turned me on to no end to know that I was making a date that would probably end with me in a sling. We agreed to a time and I met him at a busy Mexican restaurant. He was waiting outside for me and wore all black with a chain wallet. When I met him he gave me a...

Blind date

Nate's going home lonely, like he has for years. Wondering what went wrong these last few years. Cause he hasn't had a date or any one nighty stands. Its not he isn't tried cause lord knows he has, he even tried to pay once for this cute red head!!but his luck is changing he can feel it he has a blind date who said no rules. they are meeting tonight in a fancy motel. they have never met just exchanged emails she says she is sexy as hell and wanted to know if anything goes??he said that's ok and...

If Carlsberg did dates

++ This is a true story, but names have been changed ++The first time I used an adult dating site, I got chatting to a woman named Kate. I am a fan of a more voluptuous lady, so it was a BBW dating site, and Kate, in my mind, was the perfect BBW. a size 18 but with most of it on the bum and boobs, nice toned chubby thighs and a gorgeous smile. We chatted online for a few hours and then she had to go, so we shared mobile numbers and we texted a couple of times later that evening. The next day...

the first date

So this is half real. All the way up to me showing him the jiggle balls but I wasn't brave enough to put them in and he didn't suggest it because we were both too shy but after he confessed I should've gone ahead and done it or just showed him porn (I was watching it in the car on mute next to him) All names have been changed I looked anxiously at my phone waiting for the message from Ashton. Sat in the living room in my little black dress that showed plenty of cleavage and the black flowered...

The Date

Pete picked his date up in his limo. She was young and sexy. They were going to a party then back to his house or a hotel. She wore a short white dress. It was backless down to her ass crack. The front was open to her navel which barely covered her huge tits. The only part covered were her nipples. The sides were split to the tops of her legs. She was just like the young girls he dated. In the back of the limo he shut the privacy screen and began to kiss her and run his hand inside the skimpy...

Granny Kate Makes Up for A Bad Date

Granny Kate’s Makes Up for A Bad DateNow I consider myself a nice guy which is maybe why so many of the women in our Seniors Singles Club like me. I do a lot of favors for my Grannies. Last week one of my favorite Grannies Kate called me and said “I’ve got an usual request for you, and if you turn me down I’ll understand” I replied “go ahead”. Kate explained that her long-time friend Angie was coming to Tucson and would be staying at the posh Westward Look Resort. She asked if I would take her...

A recent date

Normally I don't use Craigslist because of the fakes, flakes and phonies but this guys add caught my eye and his pics did as well. I wrote him and we set a date for the following evening at 8:00pm sharp. I gave him the directions to my apartment and told him that I would be expecting him. I added a pic of the outfit that I would be wearing as a tease and to fuel his imagination. The next afternoon I started to prepare for the evening's activities. I shaved my face smooth to remove any...

THE DATE

I was having a date for the first time with Ken who I met on a sex dating site for adults. We had traded nude pictures and I wanted him bad. He was so handsome and hung like a horse. I love sex and love it wild and rough. It was my hope that he could fuck all night because I had some great surprises for this stallion. I planned to ride him like he has never been rode before. I had just broken up with Jake. Jake was twenty two and had an eleven inch cock that was thick as an arm. I knick named...

Blind Date

The desire was unbearable. She wanted sex, she needed sex badly, but the man lying beside her was sleeping. He always fell asleep before she got to bed. And even when she hurried up and found him awaken, he wasn't interested in having sex. She was getting mad from the desire. She didn't mind the lack of sex in her marriage in the past ten years, but this summer she felt the lust she hadn't experienced for many years. Perhaps, this is the first sign of the menopause, she thought. Perhaps, I...

First Date

The smell of pizza and sweat made my nose cringe when I walked out the back door of work. The long day of spinning dough, crafting pizzas, and taking orders made me ready for the weekend. Too bad Friday night looked pretty bleak with most of my wingmen out of town for the weekend. “Hey, Tombstone,” a female voice said. I looked around to see a girl with long dark hair and wearing an apron. She obviously worked at the hotel across the street. She was walking across the parking lot. I didn't...

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