*It’s been awhile guys! Life’s been wild, but that means I have a lot to share with you all :) Sorry if I haven’t responded to messages since my last post a few months back, my inbox has been flooded but I will read them I promise!
So where to begin with this one..
Back in late September, I was having one of my promiscuous “want guy’s to tell me I’m hot” kinda night so a couple of my girlfriends and I decided to hit up a bar to see if we could get drunk and maybe hook up with a cute boy or two. (Don’t judge me :3) Usually when I go clubbing, I wear pretty form fitting small dresses while bar hopping attire is usually more girl next door vibe, but sometimes I like mixing it up, especially if I really felt like fishing for a man to hook up with. So that night was one of those special nights where I gave it a little extra to doll myself out. I put on one of my go to dresses which is a really sexy black “believe it or not bodycon” dress that is so trippy! It looks like a V cut strap-less crop top combined with an X-cross cut mini-skirt. While it technically is two pieces, when put together it looks like a dress with a cut out midriff. I also applied on my “get laid” lipstick which is this mahogany red color that men seem to always notice and compliment me on.
I was feeling good about myself and so Amber and Aisha (who are my cis female friends) got to my place where we took an Uber to the bar. (Don’t drink and drive!) Amber is Taiwanese and a really prototypical good looking Asian girl with long dyed brown hair and an athletic frame. She’s basically a taller version and probably better looking version of me (:c). Aisha, who is a tall black 22 year old college student, has the looks of a model but is super duper ratchet. Like seriously, she has a mouth you would never want to introduce to your mother. She kept telling the driver to turn the radio to a hip hop station to get us in pre-game party mode, but the driver refused and she just lit him up. He was visibly pissed and Amber and I kept trying to flirt with him to keep him from tossing us out! When we got to the place (thank god we made it alive!) which was not one of our regular spots, we didn’t have to wait too long as Asha worked her magic on the bouncer. Ok… all she really did was wink at him, but still! That is some magical power she has because I think I’m pretty attractive (you can read my other stories for my description), but even I can’t just wink at a bouncer without saying anything to get into a club or bar. It takes us regular girls minutes to flirt or flaunt our way in! Stupid Asha is a witch I tell you!
Anywho, when we got in we situated ourselves in a little booth. This place was not the highest class, but definitely not your run of the mill bar. There were some fancy decor and the atmosphere was just rocking. We weren’t even seated for long when some drinks hit our table that we didn’t order. A party of guys sent it our way. We did our usual wave and thank you pout face bullshit that girls are supposed to do when guy’s buy them drinks, but none of us had any interest in that group. And so we started chatting within our own circle when that group of guys approached us and scooted into our booth. They were three college white dudes who weren’t the worst looking guys in the world but it didn’t help that the first thing they said to us was “Do you Asian ladies like the drinks?” Ya… thanks for that classification pal.
I rolled my eyes right away but we chatted a little bit anyway. Or mostly Aisha and Amber chatted. I was visibly bored with them and found myself scouting the room for eye candy instead. There was this guy leaning in on the bar counter with his worn old blazer that I for some reason kept re-averting my eyes onto throughout the conversation with those guys. He was a Caucasian man around 6’0 tall with short brown hair that matched his slight scruff excuse for a beard. I have a thing for guys with that look apparently >.<
I don’t think he noticed me but one of the college guys was seriously trying to put some moves on me and I excused myself to go the lady’s room really trying to escape. I actually walked over to the counter pretty close to where the guy I was ogling was sitting and that was when I kind of started getting butterflies in my stomach because no matter how many times you play at a bar, meeting a new guy is always like “OMG x_x!”
He didn’t say anything to me but now I saw the outline of his chiseled jaw and the edge of his blue eyes and I thought to myself “Dammnn, I so want to sleep with this guy tonight!” So I leaned in slightly over the counter arching my back as seductively as possible and asked the bartender for a Fuzzy Navel. She started making the drink and I think he finally noticed me and broke the ice.
“Fuzzy Navel eh? What is that? Sounds like some kind of stomach disease.” He said with an unexpected gorgeous British accent. I genuinely giggled at his remark. I don’t know why I was so smitten with him, but he certainly had a very sexy British vibe going.
“It’s like an alcoholic lemonade that tastes really bad, but it gets people’s attention when you need to.” I responded coyly to him. “Yes girl! That was a great response!” I congratulated myself in my head.
“Oh sorry, did I prevent someone from getting your attention?” He fired back at me. Shit… I didn’t know how to respond!
“Um..”
“I’m just joking. Here, your fuzzy navel is on me.” He said as he signaled the bartender to add it to his tab. “Although inspecting your pierced navel, it seems quite lovely to me.” The British man responded as he eyed my body.
Smooth. Okay, he was certainly flirting with me!
“I only let doctors inspect me you know.” Yep… maybe the alcohol was impairing my flirting skills.
“Good thing for you I’m a doctor.” He said in the coolest way possible. This guy must have watched a lot of George Clooney movies.
“I’m not blonde. At least not right now!” I had a platinum blonde bob cut last year. Clearly some of the dumbness of being blonde remained in me.
We continued to test the waters with each other for a while and I found out that his name was Wallace and that he was 47 years old. Yep. I totally thought he was 30. He looked good. REALLY good for a 47 year old doctor. He went through a divorce a couple of years ago and moved to the States to work with a colleague. Okay, he won me over. Tall, rugged smile, babe face, pretty fit, and a doctor… Yep he was getting in my pants tonight.
After about an hour of getting to know one another,
“You know you did say you’d let me inspect your body earlier.” He proclaimed without any shame. Wally, you sly dog.
“Funny you mention it because my lips have been a little twitchy the past half an hour. Maybe you can check it out for me doc.” Okay yes this was turning out to be a cheesy romance story but most of the time when you’re getting buzzed on the verge of drunk, you say cheesy things at bars!
“I know just the fix for that.” He said as he leaned in and kissed me. His stubby facial hair pricking against my skin, actually felt really good. It added a jolt to the kiss. Wow…
Both my hands magnetically pulled to his face, clamping it for leverage. We kissed, exploring each others lips for a few minutes before things ramped up and I slid my tongue into his mouth. His hands explored my bare back and I could feel the coldness of his fingers from holding his beer.
“Do you want to come to my place?” He whispered in my ear. I nodded and he took my hand and we booked it out of there. Wally drove us to his house and of course I texted my girls to let them know I was doing something tonight. They all knew I was going to the bar to get laid anyway.
Wally’s house was a typical suburban 2 story home that was soooo cliche. It was clean, it was hard wood throughout and it had a diamond chandelier which didn’t fit in with the rest of the home. You can tell it was missing a woman’s touch in the home decor department. As soon as we walked into the front door, Wally closed the door behind him and cornered me on it. We looked into each others eyes for such a short second and boom all that built up sexual energy we established just exploded out as we made out with rapid progression.
This time his hand slid down the backside of my skirt and groped a big chunk of my ass. I couldn’t help but let out a moan. He lifted me and all of my 5’4 body seamlessly while kissing me, all my weight being supported by his two firm hands grasped on my ass. It’s so sexy when a man exerts his god given strength to claim his woman. Wally carried me up the stairs in that position, and it took us a few seconds to get up there as our lips just could not part.
We made it to the top of the stairs and he plopped my dangling body through one of the doors of what I assumed was his master bedroom and onto his king sized bed. His bed wasn’t made. I notice stuff like that. It’s a pet peeve.
On my back with him on top of me, I reached and unbuckled his belt. He returned the favor by stripping me of my top, which literally slid right off over my head. Most women’s clothing are so easily removed. I wasn’t wearing a bra since my dress was strapless. My bare erected nipples revealed themselves inviting him to caress and give them affection. He obliged with his lips suckling my left breast while fondling the other one. His tongue moved swiftly down my body as if he was marking me with his saliva. My last piece of clothing, my skirt came off by his hands and now all that remained between him and my tiny naked body was my black laced pink tanga panties.
I was in such bliss that I was panting moderately in anticipation for his cock. He hesitated for a second. I knew he was looking at my nestled cock within my panties which were pretty much see through.
“You’re not grossed out right?” I was a little scared to hear his answer. I wanted his cock in me.
“No. You were right though. I do want to inspect your body and the secrets you were hiding.” He said as he pulled down his pants. Oh gosh, the bulge in his briefs was so damn hot. If I wasn’t blushing by now, I for sure began to turn red. This was some weird passionate mood we got going. Totally different from hook ups that I’m used to.
I reached for Wally’s cock and rubbed it, searching for the head with my fingers through his briefs. It grew bigger and bigger until it looked like it needed air. I leaned forward on my knees on the bed with him standing on the floor and pulled off the last remaining obstacle in our path. Out popped his uncut cock in which my face visibly lit up with astonishment. It was veiny, thick and probably about 8 inches. Not the biggest thing in the world, but jesus, it was super thick and going to rip me apart!
Wally pushed me down onto my back. I guess he had enough foreplay and wanted to skip the oral step. Instead, he used his hands to pull off my panties and open my legs in one fell swoop exposing my clitty. She’s a really small girl and doesn’t get too much bigger but she was excited to see Wally for sure. Wally lowered his mouth onto my clit and licked the tip of it down to my anus where he inserted his tongue all around my pussy. I tingled with pleasure and at this point I didn’t even know what was happening to my voice. He got his new fuck hole wet and ready and I knew what was coming next.
Wally lifted my legs further up compacting my body with my asshole now pointing straight up towards the ceiling. I could see his hardened cock approach my pussy. Then I felt it testing my gate, rubbing gently on the rim. He was ready. I took a deep breath and in his cock went. I let out a loud cry. It hurt. He was sooo damn thick!
“Are you okay?” He asked considerately. He’s sweet.
I was breathing heavily but said it was okay to continue. Wally slid his dick in half way. Pulled it to the brink of pulling out and then rammed it all the way in my body.
The first thrust was the worst. A few tears came out of my eyes. My pussy stretched to match the size of his cock and I slowly began feeling so much sensation. Clasping for gripe, my asshole couldn’t help but tighten with each thrust.
Within ten minutes, I was on all fours with him claiming ownership of my body as if my body was a fleshlight for his cock’s pleasure with his manhood invading my humanity. I was letting out such disgraceful sounds like a whore in a porno lol… Oh gosh.. yea…
He laid me on my side, raising one of my legs up high and continued penetrating my body. This time he put a finger into my mouth and I began to suck it. Oh god it was hot. Thrust after thrust. My leg suspended in the air, hostage to this man’s strong dominating gripe. I came all over my belly button ring and the bed sheets.
We concluded our session with me mounted on top of him slowly riding the monster that ripped through me for the past hour or so. I really had no sense of time and to be honest I was exhausted and probably delusional from lust and pleasure. When he was ready to let out his stored up work, he laid me down again and released his load all over my face and chest. I don’t remember if it was a dream or if his cum actually tasted like it, but I felt like lemonade in my mouth. He must have drank my fuzzy navel at the bar!
I woke up the next morning snuggled with Wally. Oh my god what the heck happened last night and why is my head on this gorgeous man’s chest.
“Oh hey there. You know you kick a lot when you’re sleeping?” He smiled at me.
Wow. He wasn’t rushing me out or being weird like most guys after a one night stand. We got into the shower together and that was another um… great experience too, but when we got out I wrapped a towel around my body and went to the outside bathroom to find a new tooth brush he said I could use. When I walked out of the other bathroom holding the tooth brush, I looked up and BAM there was a person standing right in front of the door.
I screamed and then finally gathered my sight and saw this girl just standing there with the most disgusted look on her face.
“What a fucking whore.” She said in the most condescending tone and walked away.
At the time I had no idea what was going on, but Wally later told me that was his teen daughter who was 17 and just started college. He apparently didn’t know she would be home that weekend and we fucked with her in the next room that night. She must have heard everything. All that moaning and pornstar crying I did last night flashed straight into my head and my face just glowed red. Oh god.
Besides that super awkward morning, Wally gave me an amazing fuck that I could not have fantasized or asked for more. I didn’t expect anything more with him especially with his daughter and I starting off in such a horrible fashion. He did call me again a day later though much to my excitement and we started seeing each other casually. I avoided his house for quite some time though until recently and that was an awkward night too, but that is for another day. Thanks for reading and I hope you all enjoyed another one of my super duper long embarrassing stories.
Source: reddit.com/r/gonewildstories/comments/5kziya/i_had_sex_with_a_doctor_while_his_teen_daughter
thank you for another excellent story. you’re always a joy to read.
Thank you so much for your stories! It seems like there are so few good stories from the perspective of trans women, and yours are wonderful :)
No lube?
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Another post about the shower, please! ??
You mentioned he was looking at your cock in your panties? Im confused. Great story btw. Any more please?
Holy shit that was so hot. I would love for this to happen to me.