28 I[M] Da[T]ing a trans woman now

So this maybe a bit long, and I’m going to sound like a complete hypocrite, but here it goes. I’m a pretty big guy, 6’2 about 180 lbs, physically fit, not a bad looking guy, plus chicks dig my job. Anyways, I’ve been going to my hair stylist for about 4 yrs now. She has her own salon, about 2 months ago, I walk in like normal, usually packed so I sign in, I sit at wait. She smiles at me and we have our usual small talk. She introduces me to her niece, who’s now working with her and says I should try her as she has about 3 ppl in front of me.
I immediately notice how attractive her nice is so I quickly say what the hell. She tells her niece take care of my favorite firefighter, he is my favorite customer. I sit in her chair, and she begins to cut my hair, we have small talk and what not and I’m kinda really digging her. She finished it up and then asks if she could take a pic and post it to her Instagram account. I don’t mind and asks if she can tag me which I allow. So that happens, 3 or 4 days go by and I decided to get on Instagram while bored at the station. I see the notification and click. I notice get profile and follow, I look at her pics and like fuck shes so sexy. I notice a few pics of her with LGBTQ shit, me thinking she was with one of her friends. Anyways days go by and I kinda stalk her profile. I end up getting drunk out one night with my friends at the bar and notice she’s posting to her story. I decided to slide into her dms, but I kinda did it discreetly.
“Hey, (we’ll call her amanda) are u free next sat, I really like the cut and wanted to make an appointment.” Amanda-“Yeah, what time did you want to come in?” Me-“Anytime you’re free, I’m sure you have a lot of clients” A-“Just let me know I’ll make time for you so you’re not waiting” Me-” About 1 ish? I get out of work about 9 am and tend to sleep till about then” A-“Sat at 1 is great ?” Me- “I’ll even bring you lunch ???” so from there we continue to text throughout the night, as I got more buzzed, I got braver and just told her how beautiful i thought she was. We were sending pics to each other (nothing graphic) throughout the night so I got the vibe that she didnt mind. Anyways I’m not going to lie, I got home and was stroking my cock to her pics, while texting her. I took the plunge and asked her out the next day. She kinda bounced around the question a few times and again I asked her out. She tells me she’d love to, but I may not want to, I ask why and boom she hits me with it. I had no idea. I don’t respond to her for about 10 mins, which was weird cuz during the night it was a few seconds to a min or 2 between messages. I keep looking at her insta and decided to say fuck it. I told her I still love to take her out.
I pick her up and fuck she was looking so good. Jeans which showed off her nice fat ass, nice tits. We end up at buffalo wild wings to watch some college football and have some drinks. It really eased the nervousness for me, I loved how she caressed my leg, would snuggle into me I’d wrap my arms around her. It was great. We were sitting at the bar, when I notice my co worker walk in, I’m freaking out, but trying not to show it. He sees me and comes over, we talk and he introduces himself to her and she played it really cool. We pay and decide to catch the last game at a dive bar. As we walk out, i’m holding her hand and open her door. As shes getting into the car, I pull her to me and give her a kiss, she puts her hands on my face and kisses me back. My hands go from her waist to her fat ass, culling both cheeks. We break the kiss, I spank her and she gets in my truck.
We get to the bar and chill for a bit, both having more drinks and my hands all over her ass. She asks if I want to go to her place for a movie, of course. We get to her apt, I’m buzzed and really into her so the nerves are completely gone. She goes to her room and comes back to her living room in a tank top, no bra, and some super small booty shorts. She sits right next to me on the couch. We put on a movie, but are more so making out. She ends up unbuttoning my jeans and whipping out my 8 inch cock. She is stroking it as shes lowering my jeans to my ankles. She gives me a kiss as she’s stroking my cock, she asks if I want her to stop. Omg fuck no baby. As I sit on the couch she lays across the couch with her head in my lap as she starts to suck my dick. Omg it was definitely the best fucking blowjob I’ve ever had. I play with her hair, put the TV on mute because I wanted to hear her slurping on it and wanted the continue seeing her suck my dick with the light from the TV. I have one hand on her head guiding it, my other hand on her back moving to her ass. I caress her ass, slide my hand in her shorts. Her ass was so soft, I tugged down her shorts with her panties, as she continues to suck on my dick. I caress her ass, sitting there enjoying the service shes giving me. My balls tighten and I can’t hold it any longer “baby, imma cum” i hold it for a few more seconds as she doesn’t stop. I shoot my thick load down her throat, she then cleans me up. I sit there a bit spent, she sits up and I notice her large clit, she has a small dick, which actually kind of works out, cuz that’s obviously not what I want. We go to her bed room and cuddle a bit, we talk about her head game and just have good convo for about 30 mins. I pull her to me and kiss her, she sucks my cock again and get me rock hard. I ask if she has condoms, she gave me one as she put it on me. She asks if I’ve ever had anal sex, I haven’t, she tells me to slide in slow and let her do the work.
We spoon as she reaches around and grabs my dick, she slides it in, I grab her hips and we rock back and forth a bit. I’m finally fully in her as I kiss her neck and back. We start to slowly fuck, she sounds so sexy. We end up in doggie, which drove me fucking wild, hands on her ass going to town. Then she rides me that’s where I lose it, she rides me till i cum. I was using a condom obviously. I’m going to sound like a hypocrite, I’ve never liked transgender people, i don’t mind the gay community, but i just feel that the transgender community tries to get everything catered to them. I’ve been consistently seeing her for about 2 months now, I’ve brought her around my friends, dates, people. Nobody knows, which is good, she seems to be okay with it. The sex is so fucking amazing, best sex ive ever had. I know I’ll probably get some shit talked to me, but who cares. I have pics of her. Kick me if you have any questions chriswhite1996

Source: reddit.com/r/gonewildstories/comments/ddq8y2/28_im_dating_a_trans_woman_now

2 comments

  1. Great story ! Just curious, is she post op? I’m confused by what you said about her having a large clit? I’m a woman btw, no judgements but so hot what you wrote

  2. I think it sounds like she’s lucky to have such a hot and accepting man! Good for you. We need more men that aren’t all fucking scared to date women that aren’t cis.
    Also, we don’t want to”get things our way”. We just wanna live a normal life without fear of being murdered ☺️

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