Posting this for a guy calling himself First timer!

Hello guys. I don’t have an account on the chat board but I do want you to post the following Story for me. It actually happened a few weeks ago.
Thanks. FT.

So, as we all know Valentines day is the day of love. But more specifically it’s a day to celebrate the forbidden love. But we all just see it as a day of flowers and candy and such for your girlfriends and wives and who ever is special in our lives on that day.
Of course the same for me. I was and still am dating a very hot GG. For those of you who don’t know, that means genetic girl. As every year I planned a nice evening in a great place to eat. Flowers and all. I am after all a bit of a romantic.

We arrived to dinner and we were late. Hair issues apparently and also not knowing what to wear from the two thousand dressed and outfits. Oh and lets not forget the fifteen minutes of picking out shoes.
Of course by the time we arrived there was a line of people. I decided to push my way to the front so I could speak to the Hostess. With a quick 50 into her hand we were promised a seat within 10 to 20 minutes. Based on the two plus hours others were being told I was happy. I whispered to the girl I would give her another 50 if she could stick to that time frame.
As I was making my way back to my girlfriend I brushed by a rather tall woman. She was wearing a super sexy short red dress. It was very low cut in the front and showed a LOT of cleavage. With long brown hair a set of full lips painted a perfect matching red, she was quite a site. She smiled at me when I brushed by because my shoulder pushed gently against on of her big boobs! Of course as I walked back I looked over my shoulder a couple of times to see this beauty. She kept watching me and I kept watching her.

Finally we were called to sit and I looked for this woman as I went in but she was no where to be seen. So we were seated and ordered a drink. The food as always was amazing and the ambiance was perfect for a nice romantic evening. Just as we were finishing our main course the beauty from the line was seated at a table directly behind my girlfriend. She was facing me but at a slight side so I could see her completely. She smiled as she sat down. Oddly she was sitting with another girl that was dressed similar to her but not quite as attractive. Lesbians was the word that popped into my head. For some reason that made me sad. I guess I was more into her than I thought.
As I was eating desert and chatting with my gf, I happened to notice this woman at the other table looking at me. When I looked directly at her, she smiled and gave me a little finger wave. I smiled back but could not return the wave.

After a few drinks and chat my gf excused herself to the ladies room. I stayed and continued to sip my drink and wait. I was looking around the room and trying not to stare when a waiter walked up to the table. Due to the fact I had just finished my drink I was expecting him to offer another. In stead he put down a fresh drink. Next to that he laid down a folded piece of paper and tapped it twice then walked away. I looked at the paper and then up for the waiter but he had already left the area. However that beauty from out side in the line was staring at me and she nodded as though I should open the paper. So of course I did.

On the paper was her phone number and her name! Gabriella. But also a question. “ Do you like women with more?” I looked up at her with a confused look on my face. She held up her right hand showing me the back of her hand with her fingers pointing to one side. Then with her other hand, she hung her index finger just below that in the middle of her hand. It kind of looked like a flag with a pole in the middle but I was still confused. So, being the simple guy I am, I just shrugged. She took a quick look around and then making sure I was watching her she took one hand and reached under the table and pointed up her skirt!! I was of course quite surprised by this but still really had no idea what she was trying to communicate. So, I shrugged again. To my surprise, she pulled her skirt about 3 inches up and reached inside her panties and pulled out a COCK!

Yes, you can imagine the surprise on my face because I had no idea she was trans. And not that I am against trans but I had never met a girl like her before. She of course put her panties back in place and just smiled when I smiled back and put her number into my pocket. Right at that time, my gf returned to the table. We paid our bill and left. I of course gave the beauty in line another smile and nod as we walked out.

Tomorrow I will call Gabriella and see if I can’t meet with her. Once I do, I will send another letter and let you know what happens. Wish me luck.

First timer.

We got another email from " First timer ".

I just wanted to update you and let you know that I will be going on a date with Gabriella this week. I She said that she will confirm with me on Wednesday for a Friday night date!

I will let you know by Monday what happens with as much detail as I can.

Cross your fingers for me guys!



Well our fingers are crossed that we get a hot story from "First Timer ".

Guys, I got the update and will post the rest of his story soon.

Ok guys below is the update we have been waiting for. I am guessing that with all going on it was just a time issue for him to send it to us.


Well I finally got that date with Gabriella. We had a couple of back and forth conversations on whats app and made a plan. It was going to be a whole day of fun. So below is basically what happened.
I drove to pick up Gabriella on Saturday morning. It was nice and sunny, and about 10am. We had planned a day completely. First was a late breakfast as she said that she really enjoys sleeping late. So I picked her up and drove to a little place I know called Juans Bean café! It’s a nice and quiet place with about 8 tables. Its also a little on the dark side as the walls are painted coffee brown and the lights are yellow instead of white. Yes it has windows but the porch cover shades it quite nicely.

When I pulled up to Gabriella’s house. I was a bit on the nervous side. I was wearing a pair of walking shorts, a nice pull over and loafers. I was dressed for a day on a boat. I walked up to the door and reached up to knock. She yanked the door open and almost jumped into my arms. I of course returned the hug. When she pulled back, I looked at her I guess with a quizzical look as she then explained that girls like her often get stood up. She also said that she knows I’m a first timer with a trans and that made it even more likely that I would not show up. I gave her a little kiss on the check and said “ shall we go?” Then motioned to the waiting car. She locked her door and I took her hand interlacing my fingers in hers and we walked out. I also noticed that she was carrying a big bag and inside I could see a pair of white keds. That was when I noticed she was wearing small heels and how short her sun dress was.
I opened her car door and she was careful to fold her more than short dress under her legs as she pulled them into the car. I also noted how long her legs were. Honestly, I almost started drooling thinking about being between them. But I shook it off and jumped in.

I started driving and she asked if she could turn on the raido. Of course I said yes and she tuened it to a station that plays mostly Latin love songs. I took that as a good sign. The drive was about 10 min with traffic and we chatted a little. Just little things about who we lived with, who I was with the night we met. That sort of thing. But by the time we arrived at Juans her hand was resting gently on my leg.

We Sat down at a back table in Juans and ordered coffee and each a breakfast plate. I also ordered sandwiches to go for the rest of the day. Gabriella looked at me a little funny when I did so I told her the rest of the day would be sent sailing. My friend had lent me his sail boat and it was stocked with drinks but we needed to bring our own food.
After eating Gabriella excused herself to the bathroom and when she came back I realized her breath was minty fresh. Then I cursed myself for not bringing a tooth brush and now having coffee breath! When paying Juan slipped me a package of gum so I tipped him an extra 10 dollars. He had just saved me!

The drive to the marina was another 10 minutes and we had a nice chat on the way. Talking about where we grew up and things like that. The entire drive to the marina Gabriella had her hand on my leg. She also had her legs up on the seat folded under her. And this gave me a nice view of her legs and thighs. I have to admit that it was exhilarating to see her smooth skin going up under her skirt. Wondering how I would react if I was able to take her dress off of her. I already had it planned out in my mind of course. I would slowly run my hands up her legs from a kneeling position. This way I could look up at her.

The boat was sitting waiting and because I had already spoken with the marina, the outboard was at idle when we stepped on board. Gabriella sat down right away and took off her heels. It was a little disappointing to see them go but I did have a nice flash of her panties. White cotton by the way. The on went the keds and she was ready to go with a big smile on her face.
I told Gabriella to relax and look around while I piloted us out of the marina and into the bay. Then it was time to set the sails. The way out was a bit slow going and the entire time Gabriella was down below. I was hoping that she was not sick. We had to pass through the wake of a couple speed boats that were not exactly traveling at the speeds they should have been.

The sail boat is quite automated and getting the sails up and working was a breeze. When I cut the outboard I heard ice tinkle as it fell into glasses. Gabriella cam up the steps just a min later with two glasses in her hands. Both held what looked like orange juice with ice. I noted that the top of her dress was now unbuttoned in the front showing her cleavage. And If I had not yet mentioned it, she has pretty big boobs. I would say at least a D. So, the site was quite impressive and also sped up my heart.

I had charted a course that would take us 2 miles off short and then turn us south to follow the coast. That meant we had the time and ability to just sit and chat. Lucky for me Gabriella was already sitting in an are that gave us both room to sit side by side but still move around if we wanted. Which I wanted very much. The distance I had charted would give us a lot of privacy!
As things go we sat for about 15 minutes making small talk and sipping our drinks. Oh and yes I was right it was orange juice with a healthy dose of Vodka and a twist of lime. It was amazing and had me relaxed really fast. Like I said I was a bit nervous. When I finished my drink I offered to make more. She put her hand on my shoulder and said “let me”. As she stood up, she leaned down and kissed me. Her lips we so soft and hot I could feel my cock start to get fat and ready. Then she was gone. Down the steps and into the area below. Once again I heard the ice hit the glasses and this time the liquids pour. I kept looking out over the ocean and enjoying the view when I realized that Gabriella had not returned to the deck. So I went looking for her.

She was not in the galley where I last heard her moving around. Neither was she seated on the sofa or chair adjacent to that. Then I heard the soft latin music coming from the master sweet. It was only then that I noticed the door was open now. I walked down to the door and found Gabriella laying on the master bed. She had her shoes off on the floor and to my surprise her panties were laying next to them. But she was reclined back and had the edge of her dress shoved down between her legs with her feet crossed. She motioned for me to sit on the bed next to her in basically the same position. I think I almost jumped on the bed but I don’t really recall. But I might have because I remember her giggling a little.

Then things turned serious. She looked me in the eyes and said she needed to have an important conversation. She explained that so far the day had been amazing and it was not what she expected. She explained that usually a guy will pick her up, offer her some token meal or excursion and then take her to a motel. They just want to fuck. So when I planned out a day like this she wanted to make sure that I understood what it was to date, have sex with and love a transgender girl. I told her honestly I did not know how far things would go. And that my plan had been for a nice day out, chatting and enjoying life. I also said I was aware of some of the issues and things that can and could happen. But I did not expect anything from her.

Then she kissed me. But this time she put her hands on my face and began to move them down my body. She touched me like any woman would but for some reason I was on fire from the kiss. I wanted to go slow. To keep my cool. But I realized it was not working. Because all of a sudden I felt my cock stiffen like it never had before. The head of my cock was pushing at my zipper and I thought that I would explode as she traced the shaft with her finger nail. That of course made me even harder if that’s possible. Then I ran my hands across her chest. Feeling her breathing increase and become deeper. As I pushed the top of her dress more open I started kissing her neck. Slowly working my way down to her nipples. There of course I paused. Kissing and sucking gently. Her nipples were medium size and getting hard as I kissed them. The pink was so sexy and her nipples tasted so refreshing.
By this time she had already worked my belt loose and had my shorts open. My cock was in her hands and throbbing. The top of her dress was down but I noted she still had her legs crossed and that was when I realized she was most likely hard as well. But keeping it hidden to not shock me. I wanted her as relaxed as she could be as well, so I traced my hand down her side. Crossing her hip slowly and then down her amazing leg. Then I started my hand going back up her leg almost like I had thought about it earlier.

When my hand pushed her skirt up I felt her take a bit of a breath deeper than she had been. By this time of course we were both breathing fast and deep. With her pulling on my cock and my hand up her skirt it had gotten nice and warm on the bed. I slowly moved my hand around on her thigh and across her ass. Then back to the front of her leg where I gently pushed her legs letting her know I wanted her to un cross them. She resisted at first but with a soft moan opened her legs slowly. I felt her cock start to move forward as she had tucked it down really hard. Honestly I became a little shocked and a little embarrassed as her cock slid back up and into my waiting hand. The shaft was as hard as mine but a good bit longer. The head of her cock was hard and throbbing. I could tell she was really excited.

We both did a bit of fumbling around to get the rest of our clothes off and that was the first time I was able to see her completely naked. Gabriella had soft creamy skin with just a touch of coffee color. Her boobs with big and round and almost perfect with medium soft flat nipples. The way she was now laying on her back, her tits were standing straight up. Her hair was fanned out above her head and it almost made her look like an angle. With curvy wide hips melding into her shapely and somewhat muscled legs. Her tummy was flat with a hint of muscle as well. But what really caught my attention was her cock laying hard and flat against her belly. I was kneeling on the bed just above her. My cock was standing straight out with a drop of clear man lubricant about to fall. Her cock was softly covered in it as well from me stroking her. It looked like her cock was oiled.

I laid down on top of her with our cocks side by side smashed between our bodies. I put my lips to hers and parted her lips with my tongue. The kiss to both of our breath away. She then whispered in my ear that today was going to be slow paced. And that we would not go all the way. Then she took my cock in her hand and started stroking as we kissed. With her words I realized that I needed to show her my interest was more than just for a quick fuck. That I also had enjoyed the day and wanted more. More dating and fun like we had earlier and of course more of this. So I did something I had never ever in my life contemplated.
I started kissing down her neck. Once again crossing her beautiful and firm tits. Of course I paused there to caress her nipples with my tongue and teeth. When I stopped there she made a move to bring herself down but I stopped her. I kept her in position. I wanted to show her that I liked her. That I wanted more and I was willing to do what I needed to do to make her happy. So I started moving lower on her body. Kissing her tummy and down until I reached the head of her cock.

I kissed the top of it. Licking the clear cum lubricant and spreading it down the shaft. I licked all the way down and then started back up gently biting and pulling on her cock. When I reached the head of her cock I took a deep breath and took it into my mouth. I did not stop. I took it down as far and deep as I could. Closing my lips and feeling the shaft move in and out as my head went up and down. I could hear her moaning and gasping when her cock first entered my mouth. I did not know really what I was doing because I had never done it before but I now know I was doing it right. After no more and a minute of her cock sliding in and out of my mouth she pulled my head up just enough for her cock to pop out and she exploded shooting her load across her tummy and up onto her tits. He ejaculation was so hard the cum almost hit the pillow next to her head. Honestly I have never seen someone unload with that much force. With her back arched and her tits straight up in the air, and her left hand still holding my cock I was not able to control myself any longer. My orgasm was just as hard shooting my man cream across her beautiful thighs and covering her cock and balls in hot sticky cream. I guess I was a little loud as well because she then pulled me up and kissed me. Telling me it was so hot and amazing in soft little whispers.

We laid on the bed together kissing off and on and touching each other for what felt like a few minutes. It was actually a couple of hours. I noticed it starting to get dark so I had to rush to turn is around.
We got home late. But she was very happy and chatty through the rest of the day. Gabriella promised we would see each other again the next weekend and that things would be different. Slower and more fun and that she would be slow and gentle with me.

But I think I have more rough ideas with her. But I will tell you about that date another time.