u/Illustrious_Clue2183

Hey there, me, Jake (28) needs to talk about this.... I met Hayley (26) on a dating site a few weeks back, and we seemed to really hit it off... I asked her out on a date and she wanted to do something casual like drinks and dancing, so we went to pub style restaurant and then dancing.... we had a few and ended up kissing pretty good in the dance floor... around midnight we went outside and we just started making out away from everyone and felt some hard press against me and I just kind of ignored it.

She asked if I wanted to come back to her apartment, so I happily did..... we took a cab back and she said "before you come up, I want you to know I am trans, I still have yenno" and I don't know if it was the drinks, or curiousity, but I just kissed her and went upstairs.

We got up to the apartment and she grabbed me a drink, and we just sat and chatted for a bit, till she sat on my lap and we started making out.

*i WANNA MAKE CLEAR SHE WAS SUPER UNDERSTANDING AND DIDNT EXPECT ANYTHING*

She took off my shirt, she took off hers and I was loving up on her... and then she went down on me, and it probably was the best blow job I have ever had in my life... I stopped her right before finishing and she asked me if I wanted to shower as we were all sweaty from the bar and dancing..

So we got to her bathroom, I get undressed and she slowly did and then her cock came out, and holy fuck... I loved it... it was a good 7-8 inches, good curve, clean, good girth ... and she says all shy "I hope you like it"

We get into the shower and clean off quick with lots of kissing etc.... and we get into bed... I was still really nervous about everything. We just started cuddling to a movie, her cock rubbing on my leg and I was loving it... then she starts kissing me neck which is getting me going..

she gets on me and were kissing and I feel our cocks rubbing together and feeling the precum drip on me and I was getting so horny wondering who it was ... she goes down on me for a bit and then she lays back and I put my hand around her hard cock and she smiles and says "you don't have to do anything you don't want to" and I said "I want to, I am just nervous, teach me" so I stroked her shaft for a bit and said, fuck it, now is the time if I am ever going to do it.

So I started kissing her neck, down her body, her tits... and I get down and I am nervous as all can be... and she reminds me if I dont want to, I dont have to.... but I was so horny, and wanted it so bad... I couldnt stop thinking about her cock... I said "i got this" and I kissed all down there,.. Doing exactly what I would want when someones down there... I started licking and sucking the balls, then licked all up and down the shaft, slapping the head on my tongue and tasting the precum.... she was telling me to touch myself while I did it... which was getting her going more... I went up and played with the head for a while because I was nervous .. and she was loving it, then I said "no or never" and put that cock in my mouth while I was stroking it... and I kept going and kept going... then decided I wanted to try to deep throat, and I did... it was hard but I loved feeling full. I kept going and she said "im going to cum" and tried pulling out and I just drowned myself in her cock... I was so "cock drunk" and loved her busting in my mouth... I swallowed it all and cleaned her all up...

She then bent over and said it was my turn, got ready and fucked her from behind, and I enjoyed every second of it... then I came in her at her request.

We got in the shower to wash off and she asked me what I thought of my first time, and I said I loved it, and she asked me what my favorite part was, and I was honest when I told her, it was sucking her dick. Anyone who knows me, knows eating pussy is my favourite thing, and I was just so full of adrenaline and loving the taste of her cock... so she said "I don't believe you" and I just dropped to my knees and put her cock back in my mouth, feeling it grow hard again in my mouth was so satisfying... then I stood up and she said "Okay i believe you"

We then got into bed, still naked... cuddling and fell asleep, I woke up around 4am to her spooing me and her cock was rubbing on my ass, and I never expected to enjoy it, but I was hard immediately, so I started grinding back on it and felt it get hard and press against my ass... she clearly woke up during it as she started kissing me and grabbing me from behind... and I siad "I want you", she said "what do you mean?" I said "I want you to fuck me" and she was very reassuring.... and said "you've never done this before.. etc"

I was so horny, and I told her to put it in me... and she said "ok, let me know if its too much" ... I bent over, she slowly started putting it, it hurt at first, but then I started relaxing, and it felt so good.. I loved feeling full. She was probably only in about 3/4 of the way, but even with the slight hurt, I felt so good, and I told her to fuck me... and she did, to the point I had my first "hands free cum" then flipped me over into my own mess, and fucked me more.. and as she was about to cum I told her to unload in me and god it felt so good.....

then we went to bed and I felt so good with it leaking out of me... we fell asleep, I went home and we have another date in the next few days.... any advice on how to give better head? I've never done it till tonight.... but I fucking loved it...

Hey there, me, Jake (28) needs to talk about this.... I met Hayley (26) on a dating site a few weeks back, and we seemed to really hit it off... I asked her out on a date and she wanted to do something casual like drinks and dancing, so we went to pub style restaurant and then dancing.... we had a few and ended up kissing pretty good in the dance floor... around midnight we went outside and we just started making out away from everyone and felt some hard press against me and I just kind of ignored it.

She asked if I wanted to come back to her apartment, so I happily did..... we took a cab back and she said "before you come up, I want you to know I am trans, I still have yenno" and I don't know if it was the drinks, or curiousity, but I just kissed her and went upstairs.

We got up to the apartment and she grabbed me a drink, and we just sat and chatted for a bit, till she sat on my lap and we started making out.

*i WANNA MAKE CLEAR SHE WAS SUPER UNDERSTANDING AND DIDNT EXPECT ANYTHING*

She took off my shirt, she took off hers and I was loving up on her... and then she went down on me, and it probably was the best blow job I have ever had in my life... I stopped her right before finishing and she asked me if I wanted to shower as we were all sweaty from the bar and dancing..

So we got to her bathroom, I get undressed and she slowly did and then her cock came out, and holy fuck... I loved it... it was a good 7-8 inches, good curve, clean, good girth ... and she says all shy "I hope you like it"

We get into the shower and clean off quick with lots of kissing etc.... and we get into bed... I was still really nervous about everything. We just started cuddling to a movie, her cock rubbing on my leg and I was loving it... then she starts kissing me neck which is getting me going..

she gets on me and were kissing and I feel our cocks rubbing together and feeling the precum drip on me and I was getting so horny wondering who it was ... she goes down on me for a bit and then she lays back and I put my hand around her hard cock and she smiles and says "you don't have to do anything you don't want to" and I said "I want to, I am just nervous, teach me" so I stroked her shaft for a bit and said, fuck it, now is the time if I am ever going to do it.

So I started kissing her neck, down her body, her tits... and I get down and I am nervous as all can be... and she reminds me if I dont want to, I dont have to.... but I was so horny, and wanted it so bad... I couldnt stop thinking about her cock... I said "i got this" and I kissed all down there,.. Doing exactly what I would want when someones down there... I started licking and sucking the balls, then licked all up and down the shaft, slapping the head on my tongue and tasting the precum.... she was telling me to touch myself while I did it... which was getting her going more... I went up and played with the head for a while because I was nervous .. and she was loving it, then I said "no or never" and put that cock in my mouth while I was stroking it... and I kept going and kept going... then decided I wanted to try to deep throat, and I did... it was hard but I loved feeling full. I kept going and she said "im going to cum" and tried pulling out and I just drowned myself in her cock... I was so "cock drunk" and loved her busting in my mouth... I swallowed it all and cleaned her all up...

She then bent over and said it was my turn, got ready and fucked her from behind, and I enjoyed every second of it... then I came in her at her request.

We got in the shower to wash off and she asked me what I thought of my first time, and I said I loved it, and she asked me what my favorite part was, and I was honest when I told her, it was sucking her dick. Anyone who knows me, knows eating pussy is my favourite thing, and I was just so full of adrenaline and loving the taste of her cock... so she said "I don't believe you" and I just dropped to my knees and put her cock back in my mouth, feeling it grow hard again in my mouth was so satisfying... then I stood up and she said "Okay i believe you"

We then got into bed, still naked... cuddling and fell asleep, I woke up around 4am to her spooing me and her cock was rubbing on my ass, and I never expected to enjoy it, but I was hard immediately, so I started grinding back on it and felt it get hard and press against my ass... she clearly woke up during it as she started kissing me and grabbing me from behind... and I siad "I want you", she said "what do you mean?" I said "I want you to fuck me" and she was very reassuring.... and said "you've never done this before.. etc"

I was so horny, and I told her to put it in me... and she said "ok, let me know if its too much" ... I bent over, she slowly started putting it, it hurt at first, but then I started relaxing, and it felt so good.. I loved feeling full. She was probably only in about 3/4 of the way, but even with the slight hurt, I felt so good, and I told her to fuck me... and she did, to the point I had my first "hands free cum" then flipped me over into my own mess, and fucked me more.. and as she was about to cum I told her to unload in me and god it felt so good.....

then we went to bed and I felt so good with it leaking out of me... we fell asleep, I went home and we have another date in the next few days.... any advice on how to give better head? I've never done it till tonight.... but I fucking loved it...

Hi there......

I am need to let this out like right now...

Me Jake (28) **making it clear ive always been bi, but never said much** and my whole friend group rented a cabin for a week. There is about 8 of us total. 6 guys, 2 girls. We are on day 4/7... It is a 4 bedroom place by the lake and I am sharing a bed with one of my good friends *dont want to name names, so well call him Jon* (27M)

well it's 3:10am, this all started I want to say 4-5 hours ago...

We were all playing drinking games, truth or dare, never have I ever.. etc...

One of the girls asked Jon for "truth or dare" and he answered to truth, she asked if shes ever thought about another man in a sexual way and he drunkenly said Jake under his breath, then said yes.

People obviously heard it, then bugged him for information.

Not going to dive to deep into the rest of the party but I went back to the room early as I was EXHAUSTED.

He shook me awake after about an hour and asked me if I heard anything from basis conversation, I said I did, he asked how I felt, I said, super into it...

he kissed me.. we touched each other a bit, got naked... then we both got nervous and stopped for a while.... so we had a drink or two, talked as friends, just had some fun as friends we've been for many years.

We were just sitting there talking and he goes "truth or dare" and I said "truth" he said "have you felt these feelings before" .... I ask "what do you mean?" he explains how he is feeling for the first time and wanting me... and I say "you've always been a great friend of mine, however, I do find you very hot" .. and he says your turn

I say "what are you feeling" and he responded with "can i show you" .... I say "yes" so he kisses me.. we start making out... we get really close and I can feel his hard cock against my leg. He then pulls back and says "truth this time, how big are you?" I say just over 7, what about you? He says "just over 8" and i say................... Prove it.

So he gets out from under the blankets and shows me his dick... and its perfect.. groomed... perfect up curve, huge, girthy, and just wow... he can tell I was staring at it and he says "do you want it?" I without thinking grab it (and this is the first time ive ever had a cock in my hand) and I start stroking it... and he's moaning, leaking precum all over my hand... and he looks embarrassed that it happened so quick.. so I rubbed his precum all over my face

I got on top of him and started kissing him, his neck, and rubbing his cock on my ass, I could feel him get harder and making my ass wet and it was turning me on so bad.

I got off as I was super overwhelmed by this being my first time and he asked me truth or dare and I immediately said dare... and he said I want you, do as you wish with this.

I then got super nervous as I had never done this but all I could think about was his cock in my mouth.

So I laid him back, super nervous.. but thought about how I would want it.. kissed down his body, licked.. etc. Started with his balls, licked up his shaft, played with the head and finally put it in my mouth.. I put my mouth around his huge cock and started sucking as I'd want it... Stroked him, sucked him for a while till I got him to cum... he warned me but I just wanted a load in my mouth to be honest. I loved the feeling of him unloading in my mouth,

He said he wasn't ready for that which I understood so he gave me a good rub and I finished.

After that we went to bed... I woke up a bit later to him spooning me with his precum cock rubbing on my ass, and I LOVED it... so I pushed back... he woke up, starting stroking me around, while his cock was rubbing on my asshole... and I told him to put it in. He asked if I was ready (wasnt fully sure if i was, but ive buttplugged lots, bring lube everywhere as thats how I masturbate) ..

I got up, grabbed some lube and told him to put it in... he was huge so it was alot to take. It hurt at first.. we were on the side, and I was getting used to it. but after relaxing it felt so good. We fucked for a few then I bent over for him and he got it in probably 3/4 and I told him to just get it in. He put his huge cock in me... and I told him to have fun as he would with anyone else.. he fucked me and fucked me and was just about to cum and I told him to cum in me..and he did.

Im writing this post and im ready to start blowing him again... this was wild... i leanred i loved this.. and sucking dick is my new favourite thing.

One time down, already love cum... in my mouth, in my ass (and its just a nice new experience)

**to those who read this long, any blow job tips for tomorrow**??

For those of you who havent seen part 1: https://www.reddit.com/r/transstoriesgonewild/comments/1t0rerz/first_and_few_times_after_with_trans_girl/

so.... I posted part 1 like 7 hours ago, but the amount of messages I've recieved asking for updates on the scenario is insane... so here we go.

After that first night, I couldn't get enough, I wanted to learn, I wanted to do better, experiment... whatever.... after the first night, I wasn't entirely sure if I loved it so much due to the alcohol in my system, so I thought I'd hit her up again and do it completely sober..... she came over to my place.

She comes by, and I was thinking of her all day, and was so horny thinking of her... so the moment she comes to the door ... I drop to my knees and start sucking like a good boy... I loved it... I was prepared when she came in... had a massive plug in...

I got dildos and plugs to practice after the first night, so I could practice... watched some blow job tutorials online and just practiced... dildo definitely aint the same as the real thing so I was so into it. I love it.

Everyone who knows me, knows eating pussy is my favourite thing... but I cannot believe how much I love sucking dick. I love it in my mouth, I love the precum, I love the throbbing.. i love stroking it and ahhhh. So i get her going with that and I say "i know you arent a big dom person but I want you to just take control of me" I wanted to feel dirty.. I wanted to be used...

She lays me back on the bed and put hers hard cock in my mouth and starts thrusting good... face fucking me, my eyes rolling back... her long hard cock going down my throat... im gagging... but taking it... shes calling me a good boy... then she stops and flips me and puts it in my ass... and starts going to town... she pauses part way through and pulls out one of my dildos... and puts it in my mouth... spanking me... talking dirty... shes fucking me so hard I came all over the bed and she flips me over right into my cum... and keeps fucking me until she busts a huge load in my ass. I love the feeling of that throbbing cock deep in me.She filled me up with her cum then immediately bent me over and started eating my ass... first time thats happened, but shit.

I feel so dirty, being a bottom.......

Hi there, I am not sure how much detail is allowed here, so I will do my best to not be too graphic lol. My name is Jake (28M) up until this story, I've only ever been with women, vagina owners.. etc... then I came across a subreddit... got home from work, was looking at porn, hit something I didn't recognize and it was a page dedicated to girls with cocks... and I got a urge for something I never thought I would.... days went by... I kept thinking of it, and going back to that page... slowly expanding.. finding t-girls masturbating... self facialing... then I got really into it and watched straight guys do it for the first time and I was getting so turned on by the idea.... I've only ever been with those with vaginas... but damn... there was some not nice looking things.. however there was a couple cocks that I just wanted to touch so bad.... I've always been a top or what not in all previous relationships, but I started thinking about been fucked and controlled and gosh... I bought a few toys and starting fucking my own ass.. walking around with plugs and beads in...

So I've still not admitted this to anyone but joined a dating site for finding trans.. couple weeks, no real luck.. then started chatting with Morgan (29F) ... we went out on a date... got to know one another etc... date 3... we went out dancing and had quite a few drinks... we left the club and made out heavily outside.... I was so horny and I felt her hard cock on me.. and she says "lets go back to my place" and I say "why don't we get a hotel?" ... she agrees but has to make a quick stop.. I don't question it...

We go to a nice hotel over looking the lake, get a room with a nice jacuzzi in it... we get to the room and make out... she says be right back... goes into the bathroom... and comes out with just a bra and thong on... her cock bulging outside the thong.. I was mesmerized... it was like a porn dick... not gross.. so groomed... im gonna guess 8 inches... probably bigger than me (confirmed after she is bigger) she had such a nice up curve... and wow.. and comes and makes out with me... and undressing me... and asks me if I'm ready for my first time... and said really reassuring I don't have to do anything I dont feel comfy with.. but I was so horny and wanted it all...

We make out more and I kiss her neck and rub her tits.... as she puts my hand on her cock.. and I was a little overwhelmed but I start rubbing it and she asks if I want to take a quick shower...

so we make out the whole way to the shower and we get it... i get under the water facing away and she puts her arms around me from behind... starts rubbing my cock and I feel hers rub on my ass.... I am so horny at this point...

We have some make out sessions in there and leave the bathroom naked... cocks rubbing together.. and she says she can bottom so I don't gotta do anything different.... ya see... I've always been a dom in relationships but I am already here so why not ... I said "teach me" and she was confused... so I drop to knees.... stroking her cock... I slapped it on my face a few times... and I look up at her... feeling her precum run down my chin... and I say "Cum for me mommy" and she looked so ready... so I start by licking and sucking the balls... I was really hesitant and nervous ... but I loved it so much... I licked up the shaft... teasing every inch... making her want me... teaching the head... licking it ... then I finally go for it and put my mouth around it... it was so big.. I am touching myself during it... I loved the feeling of it in my mouth.. I slowly start sucking farther and father down... she was giving me advice and then just started to enjoy... I was sucking and adding suction.. stroking as I went... deep throated (didnt go great for a first time) and I just kept going and she tried to pull away when she was about to orgasm and I just looked up and her and kept going... only took at 3-4 minutes and I had a massive load in my mouth... I swallowed it all and cleaned up the mess. I loved it.. I loved sucking cock.. I loved it so much.. I loved swallowing it... being called mommys good boy...

She then gets on her knees spreading her tight ass.. and tell me to fuck her... so I lube up.. and put my cock in her tight ass and oh my god it feels good.. I try reaching around to touch her and I couldnt so I flip her to her back and start fucking her missionary.. and stroking her at the same time.. and she says shes gonna come and I stop and put her cock in my mouth again and lick it all up...

She then tells me to fuck her so I can come cum... I tell her what I want... I say make me your sex doll.. have your way with me... make me ur bitch... and she agreed... and says just something if its too much... she lays me back, head off the bed and forces her cock down my throat... thrusting and thrusting.... till she goes down and we 69... I absolutely loved having a mouth full and having to take it.... she was dirty talking and nothing made me more horny than her calling me a filthy slut .... she then bends me over and lubes up her fingers and starts going to town... feels different ... but not bad, not great... adds a finger, then another... stroking me... getting me nice and relaxed.. im so horny at this point where I just say me mommy... and she slowly starts putting it in... inch by inch... hurt quite a bit at first.. but so pleasurable... I loved feeling full... after a few, I relax and take some more, she definitely didnt get it all in, but I loved feeling full like that...

Once I relax, she slowly started thrusting and it felt so good... like so good... like to the point ive never felt such a sensation... I yell mommy fuck me and she goes hard... hurt a bit but omg ... ive also never felt such pleasure.... she flips me on my back and gives my cock a quick deepthroat then proceeds to fuck me again... shes rubbing me while pounding me... and I feel myself getting there... she gives some thrusts and I just start cumming all over myself.. and stops and leans down and licks me clean as I ask for more... she keeps fucking me and I tell her to cum in me.. she keeps going as she cums... i feel that cock pulsating.. releasing what I didnt swallow earlier... I felt so good... I just wanted it to stay in there....

We then proceed to cuddle as she insists I cuddle into her... my head nuzzled into her ... shes rubbing my back and im rubbing her thigh... and her cock gets hard.. and I just play with it... for a while... and she tells me I was a good boy for my first blow job and wants to see my technique again... I have no complaints... I start and just keep sucking... I didn't want it to leave my mouth... and I ask her to 69... so we do... I loved every moment till I told her to stand up... I dropped to my knees and told her to cum on my face... I blew her more and more and jerked her, teasing her... getting it going till she lets a pretty small load out of my face.. hahah

so after this we go to bed.... we fall asleep me spooning her... I wake up around 7am.. shes still out, but I feel her cock on my ass and its getting me all turned on... I start rubbing back at her.. and shes clearly awake but I pretend im sleeping... I feel her get hard, rubbing on my ass.. when I just reach around and put it on the hole.. tell her to go for it... hurt like a bitch so she grabbed lube.... the side position wasnt great.. so I laid back for her again and took another load in my ass. Came fully hands free for the first time....

***************

that was my first time.... we still meet up sometimes... but let's say I have experimented since.. for sure. Cock is my new favourite thing.