(Hey fellow sissies ^^ I’m here to tell you the story of my first time (witch was yesterday)
The story starts by me chatting with a guy, we talked a lot and he finally says “if you want to have you first time you should really download Grindr again” (I already had one in the past but deleted it). So I did create a new account, pfp, BIO (where I obviously says I’m a crossdresser looking for his first time)
And I find this guy, another crossdresser, he was a really cool dude, he really wanted to be my first time and he had some clothes / gears to try on my. Yesterday was the day with him, unfortunatly for me (and for him) he blocked me… But I was way too horny and I didn’t know at the time if I would be brave enought again to meet someone else. So I open Grindr and there was this guy he wanted to meet right now, he gave me his number (because I was really nervous) and we agreed to meet, he asked if I could bring some female clothes, and I obviously said YES.
Once I got there we chatted on the couch and I was still super nervous about showing me in those outfit, so we played smash bros (no kidding xD). After two games he said “If you loose this one you’ll have to dress up” I agreed. And, I lost :D.
So I was like “Ok I lost I’ll show you one”, I got a pink outfit: “panty; tights; skirt; crop top;” he said I was beautifull in this, and I was really turned by wearing the outfit. He took his time but he finally started fingering my ass. I was ready !
He got naked and showed me his dick, he wanted me to suck it, but at the moment I was too nervous and said no :/. So he grabed a condom and asked if I was ready, and I was. he removed tights and panty, lubed my ass and YES he got inside, I realised it was for real this time. He started slow but quickly he accelerate, we changed position multiple time, he was controlling how he wanted to fuck me. Then he cummed i my ass with him condom.
We took a shower and chilled in couch while talking what happened, we cuddled but, he got horny again, but this time when he asked if I wanted to suck his dick, I didn’t hesitate, and I did, my got that was awsome !
We got into his bed and I started sucking his dick again. But quickly he wanted a deepthroat, so I did 😍. (Afterward he said I took 17cm in my mouth of his 19cm). I gagged multiple time, but didn’t stopped me from deepthroating! And as I was doing that he started calling me names, I was his slut. I stopped sucking his dick because he wanted to kiss, but only did we kissed but he said I was his little slut, and he spit in my mouth and on my face. I was so happy, I then quickly stared sucking his dick again, but he wanted to fuck me again. And oh my god we fucked I was so in the mood, moaning while he was inside me. I even could ride his dick. And after that he said he wanted to do a facial. I agreed, he removed his condom, stared masturbating just by my face (I was laying on the bed he was above me) and he cummed on my face, I loved it.
We took another shower, and again we cuddle on the couch, I sucked his dick one last time for him to cum a third time, witch he did. We kissed and said goodbye, I got into my house, eat and sleep while thinking if I wanted to do it again with him (I’m still questionning but it was to good I really want to).
That’s the end of the story of my first time. I think if I see him again he’ll try bondage on me cause in the bed he asked if I was ready to be tied up for him. It was really amazing, and I would love to do it again, but I also want to play with another sissy now, didn’t find any on Grindr (appart the guy that blocked me :/) I will of course post update if I do, and you can also ask any question, I’d be happy to anwser ! If there is any mistakes in my text it’s because english is now my native language sorry :/.
Goodbye now !
That sounds great darling! I’m glad you had such a fun time. Grindr can have many time wasters on it but as you’ve found you can meet some cool people on it. Best of luck ~
That’s what I noticed, as long as we are carefull about who we pick, everything should turn out great ^^
Thanks for the update, such a hot story!