I am a very inexperienced 19 years old guy and into crossdressing, also I am into women 10-20 years older than me. So on one day, I matched with that 29 years old beauty with brown hair and a great body.
I told her that I‘m specifically looking for sex and she was more than fine with that and she knew that I am into crossdressing as well. She said, she‘s very much into BDSM, which I am not. Also, she‘s a dom only. She wasn‘t looking for vanilla sex at the time, but we decided to meet up at a cafe near her place either way.
She wore a red dress with fitting lingerie.
We talked a bit about what the both of us would like to do and what are no-gos, as I didn‘t knew too much about BDSM things. We drank a couple of drinks and decided to go to her place, where we started making out on her balcony. Only kissing for first, but damn she knew what she did. We easily kissed 10 minutes, but I loved it. I was making a move with my hand between her legs, which she blocked.
As an immediate reaction, she put her hand on my leg and went upwards on the inside of the shorts. The pants were too tight for her to get near my dick, so she stopped that again.
She intercepted our kissing and said, that this would have worked better, if I would wear a skirt or a dress. I laughed and agreed. She smiled and asked, if I want to wear one of hers.
I had to think for a second, as I wasn‘t prepared for something is at all and never did anything like that with someone else with me. But in the end, I agreed.
She took my hand and led me to her bedroom and went through some of her dresses. She chose a brown thin dress and looked at me. She commanded me to take my clothes of right now, with a more dominating voice.
As she told me, I did that and she helped me put on the dress. We went back to her balcony and kept making out.
We sat next to each other and she told me, to put my legs on hers (kinda like [this](https://imgur.com/a/noRNuQO)) and we made out again. She started choking me a bit and asked me, if I liked that. As I said yes, she increased the power and kissed me again. After a couple of deep kisses, she let down my neck again.
With her kisses, she went a bit downward towards my neck and down to my nipple, with the licked and kissed. Whilst doing that, she put her hand back on my leg and went upwards slowly. She teased my dick very slightly with small touches. Then grabbed my dick and balls and squeezed them.
Whilst doing that, she asked me, if I want to go into her bedroom and get my ass fucked. Just like that.
I was thrown off a bit and needed a second to think again, but eventually agreed. She slapped my ass and pulled me after her.
She pushed me onto her bed and sat next to me. She smiled and went down to kiss me again. Slowly, she moved herself above me and between my legs.
She started pushing her hips against me and went harder on me with every bump. She licked her middle finger and went on towards my asshole and slowly put it into me. I gasped deeply as she did that and smiled at her.
She continued her hip thrusts with her hand at her hip as we kissed. Once she stopped the kisses I asked, if we want to switch over to a dildo. She smiled and agreed.
She pulled out a strap-on with a fitting dildo and applied some lube to it.
She asked if I was ready and went back between my legs.
She slowly entered my ass with the dildo and started fucking me whilst looking me straight into the eyes. I started heavily moaning, she increased the speed and power on me.
She took a short break and put a pillow below my ass and went on me again. Once she was as deep as possible inside of me, she pushed her whole body closer on mine and started fucking me again. I think I moaned as loud as never before.
She started leaning backwards and pulled myself up, now I was sitting on top of her. I started riding the dildo and she starts thrusting me again too.
I felt myself cumming soon and I said so. She said it‘s fine and i should just let it go.
I started moaning and cummed as much as never before probably.
Most of it landed on her bra and face, she started laughing. I went off of her and laid next to her. I started licking the sperm off of her face and we kissed with it in our mouths. After one or two minutes, we left it at that.
She told me to go take a shower and I asked her to join me. She laughed and agreed, under one condition: No pussy!
I agreed and we jumped under the shower. We made out a bit again but left it at that.
She gave me a slap on my ass as I put on my clothes again, laughed and said: „I hope we will see each other again soon!“ So do I.
Source: reddit.com/r/gonewildstories/comments/hh13x2/my_very_first_tinder_date_with_a_29_years_old_real