This is my first time writing here on gonewild so please excuse any mess ups in format/spelling and will see how good my storytelling is.
I am 29yo transgender Female and have been on hormones for about 5 months when this happened, its been awhile but I thought you all might like it. I know some of you love to know the details so I am about 5ft8 and 135 pounds and have very dark brown if not black hair with deep green eyes and now sport a small 34B’s. This story is more about the lead up that got me there so skip ahead as wanted.
It was just another day in March and I was going out to lunch with a male friend “who I will call Jon” of mind that I know from a mutual hobby/passion. We just went for a quick bite to eat to a little pizza joint right in town from where we enjoy our hobby. We both ordered and I actually fought with him over the bill and won only by saying he could take me to dinner. Now Jon knows I’m trans and preop as he has known me longer as my deadname…
Lunch was good and he made reservations for dinner at a really fancy place just out of town. Btw a little backstory he is previous student of mine in the hobby we enjoy. Jon is about 6ft2 and probably 200 pounds with dark longish hair and hazel eyes. After lunch we went back to go enjoy more of our passion and I had another student to meet.
Later that evening after wrapping up bit late we both enjoy a quick 420 dab before having to be told I have 20 min to rush and get ready. Now at the time I had only been living full time for a couple of months and I was no way quick at getting ready yet. I’m not sure how but I was able to take a quick shower, thank god I shaved that morning change into a beautiful red cocktail dress with black highheal pumps and reapply a quick makeup job.
Go figure he was late getting to pick me up by about 10 min and I had time to get my makeup a bit more on point. He picked me up in his rental car as we was visiting from out of town and quite impressed at how well he cleaned up. He was defiantly a gentleman and opened the door to car for me. I blushed a bit as this is something I’m still getting use to even now but absolutely loved it. It was a good 45 min drive to the restaurant a place called Ocean Prime.
We pulled into the parking lot and could already tell this place was probably the nicest place I have ever been too. He again opens the door for me and the receptionist showed up back to our table. When our waitress came Jon asked for the wine list and the waitress went to go get the sommelier. Jon asked what I liked to drink and I reminded him I’m not much of a drinker and especially don’t like wine. He said I probably hadnt had a good enough wine and I told him my parents are wine snobs so yes I had tried some good ones. I told him I would at least try what ever he got though. He ordered some chilled white whine cant remember what but it was awful and biter. Don’t know how expensive it was but from the restaurant and knowing him was probably close to $200-300. He asked if I wanted something else to drink and I reminded him I prefer 420 to alcohol and asked if he was trying to get me drunk and winked. I folded and ordered a lemon drop my go to drink if I drink.
He went nuts ordering like 5 different appetizers, from sushi, lump crab meat and even some Wagyu beef! For those of you that don’t know what Wagyu beef is its more expensive then Kobe beef. I was in heaven on my first bite of it as it proceeded to melt in mouth! The best comparison I can give is the candy bacon of bacon.
I finished my lemon drop about the time our meal came which is weird as usually I don’t even finish a drink as I can always taste the alcohol but what ever expensive vodka they used was just like cane sugar and delicious! I’m normally a bit of a picky eater but the meal was amazing and was the first time a chef made me want more veggies! At some point another lemon drop arrived and I was feeling nicely tipsy and figured it didn’t matter if I had more as I didn’t have to drive. When dinner was done we were both stuffed but somehow ended up with this really amazing chocolate and peanut butter dessert that was like a home made Reese peanut butter cup but on crack. When it was time to go I finished my drink and we headed out.
I was a bit worried as we got up as I realized this is only my 3rd time now being drunk and the first time being drunk in heals! Not sure how aweful I looked leaving but managed to get to the car without falling just a a bobble or 2. It was about 10 min into our drive back to my place and I started feeling funny. Now he is not what I would call a slow driver and I wasn’t sure what I was feeling but I turned towards him and looked at him. Now I was worried I was going to tell him he needed to stop so I could throw up but I quickly realized this is not what it was! For the first time since knowing him in the past 5 yrs or so he was actually attractive! I turned back to looking straight out the window shield as my mind stared going crazy with a million thoughts the 1st one being was wait was this a date? Now prior to this I always identified as Bi but never gone out on a date with a guy. Now as my mind is racing I go from questioning if this was a date to if it was and he makes a move what do I. Well it didn’t take long as he is very handsome and a gentleman, funny and we enjoy a major passion for our hobby, to go yeah I don’t care what you want but if you play you wan it you will probably get it. I started fantasizing about giving my first blow and what to even do. I realize I can put my past experiences from receiving them to use and probably at least fake a half way decent blow job. I start thinking about how big his cock will be and if I can take it then realize its almost defiantly circumcised as his family is Jewish. Then I start wondering if I can take him as I haven’t had anything in my bum in a little while. I start thinking of him slowly pushing into me as I feel myself get stretched out and my hole actually spasms! The fantasizing continues as I think of him taking me from behind in doggy and the next thing I know I can feel a warmth swelling upside and feel myself start to drip and get my panties wet! I couldnt believe how turned on I was and as I fantasized about him pulling me over and taking me right there it happened! I started having an almost full body orgasm right there in the car as he drove. I had to bite my the right side of my lip pretty hard as I tried to not make it audible, it took everything I had to not spasm out of control and show my orgasm. I looked over and it seemed like he hadn’t noticed and I smiled. It took almost the rest of the card ride for post orgasm bliss to subside! I was in awe of what had just happened! Now I know some women are able to think themselves to orgasm but the % I thought was so tiny and never though HRT would get me there.
When we pulled into my house we both got out and headed to the door. We said goodnight and unfortunately I only got hug out of him but looking back it was just 2 friends grabbing dinner as he was totally hitting on the waitress and isnt interested in an intimate relationship as I’m Trans. O well I know I had a much more awesome night then he did and maybe one day I will tell him about the unintentional orgasm he gave me.
FYI I think its a crying shame for guys to get circumcised, its genital mutilation which we get on other cultures for doing to women, it totally reduces the pleasure and I for one am glad my parents did do that to me as my SRS result will be better.
PS guys: I’m so sorry society has everyone so homophobic that must of you will never enjoy a prostate orgasm. It was the only way I could achieve a full body orgasm pre transition and now on Hrt my other orgasm have turned to full body ones too!
Source: reddit.com/r/gonewildstories/comments/6f9bg3/the_first_time_imtf_had_an_orgasm_just_by
Very hot ❤