Finding My Dream Wo(man)

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"You were amazing in that video," I exclaimed.

"Oh, it wasn't difficult for me. With my background, I've got plenty of pent up sexual frustrations. When I was acting in front of the camera, I could totally let myself go. Besides, it was the only sex I ever knew. A girl like me can't exactly meet a regular guy at the local bar and end up in his bed without causing one hell of a commotion."

"So what has your sex life been like now that you are out of the business?" I asked.

"I go through a lot of lube and watch a lot of porn," she laughed. "My safest date is with my right hand. Most guys don't take too well to my little surprise."

"But I'm sure you could find the right guy. Somebody who understands and is actually excited about your special talents. And trust me, nothing is "little" about your surprise," I said. "I mean, you've got me beat by a couple of inches."

"I hope I can," she sighed, batting her big green eyes at me, and making my heart skip a beat. "And don't feel bad, baby, not many folks could measure up to what I'm packing," she giggled as she cupped her package and gave it a heavy squeeze.

"Is that why you gave me that dvd?" I asked, my eyes glued to her crotch.

"Well, a girl with a dick deserves love too, don't you think? I'm tired of hiding behind my tennis skirts. I thought it was time to take a chance."

"I'm glad you did," I sighed.

"Let's eat dinner, sweetie," she cooed as she gave me a big hug. I felt her semi-hard (I think) cock pressed against my leg and I knew right then and there I wanted to see this through.

We talked about any and everything besides her sexual past during dinner. Her sense of humor was infectious and we laughed and joked like old friends.

During dessert, she looked me straight in the eye and asked, "So Scott, do you think you can handle the Carlita in me?"

"I, uhhhh, I, well, I want to find out," I sputtered.

"Good boy, I knew you'd be up for the challenge. We'll take it slow tonight. Have you ever had any bisexual experiences?"

"A few back in school."

"What did you do, back in school?" she asked. "Did you ever get that cute little ass of yours fucked?"

"Umm, well, no. I jerked off a couple of guys, and I had a buddy that we, errrr, well, we blew each other a few times."

Turning her chair away from the table, she spread her legs and started to hike up her sexy little summer dress. "Be a good little boy and crawl over here between my legs. I'm going to formally introduce you to my girl cock."

I swallowed hard and did as instructed. I've never had any real submissive desires, but something about this sexy woman and her take charge attitude had me willing to do just about anything for her.

"Start at my feet and kiss your way up my legs. Go slow and really worship my legs."

She didn't have to ask twice. I did worship her beautiful, toned legs. I kissed and nibbled my way up, making love to her inner thighs and causing her dress to tent massively.

"That feels nice, Scotty," she cooed. "I normally wear very restrictive lycra shorts as underpants to keep my beast at bay, but I wanted her to breath tonight. You are making her very excited."

With that, she lifted her dress hem, revealing her huge erection. I was in awe. Here I was eye to eye with the biggest cock I'd ever imagined, and it was attached to the most beautiful woman.

"She likes you Scotty. Do you like her?"

"Yes, very much," I croaked. I reached out my hand and gently grasped her throbbing member. It was warm and heavy, hard as steel, but somehow still soft to the touch.

"Did your buddy back in school have a cock this nice?" she giggled.

With a frog stuck in my throat, I croaked, "Not even close."

"Kiss her," she ordered.

I did, tasting the sweet precum that was dribbling from the massive plum shaped head of her mighty cock.

"Ohhhhh, that feels so good," she purred.

"Kiss all the way down my shaft to my big girl balls, sweetie," she insisted. "Take them in your mouth and suck them gently."

I was glad that Carla was coaching me. I had rarely been with a woman that knew what she wanted and wasn't afraid to ask for it. And I was clearly out of my element in servicing her amazing cock. I needed all the help I could get.

"Take me in your mouth and slowly stroke my shaft," she said. "And look at my face as you take me into your mouth."

"You like my big cock, don't you honey?" she asked. "I can see the lust in your eyes."

With my jaw stretched to fit her big dick, I could only nod. Her tool was leaking copious amounts of fluid and I was absolutely intoxicated by the taste of her sweet seed.

"Are you going to learn how to take my entire length like a good little slut?" she asked.

I was positive there was no way I could deepthroat her entire tool, but I wanted to make her happy. I tried to force several inches down my throat, but could barely get half her length in my mouth.

"That's OK sweetie, I'll help you out. Why don't you strip down naked and let me see that hot body of yours. Then jump up here on the table, on your back, with your head hanging over the edge."

"Oh, you have a nice cock, baby. I'll put that to good use later."

With my head hanging over the edge of the table, Carla took my face in her hands and lined up her big erection with my open mouth. "Just relax, my little cockwhore and when you feel my cockhead push against the back of your throat, swallow hard and it will pop down your throat."

Fighting back my gag reflex I did as she instructed and felt several more inches of her big sword slide down my throat. I struggled to breath through my nose with her thick tool completely shutting off my windpipe.

She pulled out slowly and thrust forward again. After several minutes of this throat fucking, I felt her big hanging balls bouncing off my forehead. I had somehow managed to take nearly her entire cock.

"Good little bitch," she panted. "I knew you could do it. If I keep fucking your face like this I'm going to blow my load. Your throat feels like crushed velvet on my cockhead."

God, I wanted that so bad.

"Jump down off the table sweetie and get on your knees. I want to look you in the eyes when I fill your throat with my seed."

"Put your hands behind your back and completely submit your mouth and throat to my cock," she demanded.

As I knelt in front of this goddess, she pulled her sun dress up and over her head, revealing her beautiful body. She wore a lacy little white bra that barely held back her heaving breasts, and I could see that her dark nipples were rock hard. Seeing that giant cock protruding from her very feminine body made me want to satisfy her in the worst way.

"Do you think I have a nice body?" she asked, as she gave her erect nipple a hard squeeze.

"Carla, you are gorgeous," I replied.

"And do you like my big girl cock?" she continued, reaching down and giving her monster boner a gentle, slow stroke.

"I absolutely love it," I admitted.

Teasing me as she rubbed her cock across my cheek, she said, "Tell me what you want me to do with this?"

"I want you to fuck my face, Carla. I want you to feed me your hot load," I whimpered.

"Are you my little cocksucker? Let me hear you beg for it, cocksucker."

I thought I was going to shoot my load right there. When her dominant streak came out, I knew I needed to be her bitch. "Please Carla, let me be your cocksucker. Let me take your cock down my throat. I need to swallow your load. Make me your little cum slut."

"Good boy," she patted my head as she started feeding inch after glorious inch into my mouth.

I kept my aching jaw open wide and used my tongue to lube her big rod as she stuffed more and more into my eager throat. I kept my watering eyes turned up toward her, so she could see how much I lusted after her cock.

"Such an eager little cockwhore, aren't you baby?" she said, as she put her hand on the back of my head and forced her cockhead into my tight throat.

I couldn't respond other than to give a slight nod. I could feel her cock start to swell and I knew she was getting close.

"Oh baby, I'm gonna fill that pretty mouth of yours with my hot cum. Ohhhhhhhhhh, yea," she exclaimed as I felt the first burning jet hit the back of my throat. She slowly started to pull her weapon from my mouth, squirt after squirt of her thick jizz coating my tongue. As her cockhead cleared my lips, several long, thick ropes shot across my face, landing on my forehead, cheeks, and dribbling down my chin. I know its not really possible to "cum gallons" but I swear it felt like she had unloaded a gallon of sticky cream.

As she wiped the last few drops of cum on my tongue, she sighed, "You are such a pretty little bitch, all covered in my seed. Did you like that?"

"Yes Mistress," I moaned, not sure where that name came from.

"You do have a little submissive streak in you, don't you Scott?" she asked.

"I guess I do, Carla. At least if you are the beautiful woman dominating me."

"You're so cute. I can't wait to pump my next load deep in your tight little ass," she giggled. Leaning down, she ran her tongue across my cheek, herding her thick cum toward my open mouth. With my mouth filled with her jizz, she gave me a long, deep kiss, our tongues dancing the tango, before she stood back up.

"Swallow it lover," she instructed.

Without a second thought, I swallowed the rest of her yummy treats, smacking my lips with satisfaction.

"God, Carla, I love the taste of your cum," I honestly said.

"I'm glad," she replied. "Cause I've got plenty more where that came from. Why don't you stand up and let me return the favor."

She knelt before me, and literally inhaled my rock hard dick. I didn't last a minute under her professional technique, and when she reached around and inserted a finger into my unsuspecting ass, I filled her mouth with a huge load.

Looking up at me, she said, "I guess you liked that, huh baby?"

"Unbelievable," I sighed.

"One of the advantages of being an ex-pornstar, I guess. You could say I know all the tricks of the trade."

I collapsed back into the chair, exhausted and oh so satisfied. Carla stood up, her cock still semi-hard and oh so impressive looking. I should have been embarrassed that she was bigger than me, but the vision of her incredible tool only made me horny for more. And the way she had just serviced my rod, I knew I could still learn a thing or two about satisfying this amazing lady.

"Let's clean up these dishes," she said. "Then I'm gonna bend you over the kitchen counter and fuck that tight little ass of yours till you beg me to stop. Oh, and by the way, I won't stop, and you'll love it."

I wasn't sure I could take all of Carla, but I was willing to try anything for this incredible woman.

As we cleaned up from dinner, I watched her big swinging dick like a love struck teenager. Even soft, she was impressively long and thick. Where my dick tended to shrivel up when not erect, her penis remained obscenely large. I was literally mesmerized. A stunningly beautiful woman with a dick a porn star would give his right nut for. In the last 24 hours I'd been turned into a cock addicted slut.

"Can't take your eyes off my prize, can you sweetie?" she laughed, catching me staring at her package. "I'm so glad you are a size queen. Turns out most men are if they open their minds about it."

"I know I should be conflicted," I responded. "I mean, you are a gorgeous woman, but I can't help feeling I should be repulsed by what is between your legs. Fact is, I'm the exact opposite of repulsed. I want your cock more than I've ever wanted anything in my life."

"Don't worry baby," she cooed. "I'm gonna give you all the cock you can handle." She reached down and gave her dick a quick tug, her pretty little fingers dwarfed by the thick shaft. "I love fucking a tight ass for the first time, watching a man convert to a total cock whore. Don't be too scared; I warn you it will hurt at first. It will hurt a lot. But inside 5 minutes, you'll be begging me to fuck you harder as you thrust back against me, trying to get my cockhead to stimulate your prostate just right. And don't worry, I like getting anal as much as I enjoy giving it, so you'll get your turn too."

I had fucked a couple of girls in the butt before, and it was always a miserable experience. They hated it and I'd always try to cum fast before they insisted I pull out. But I'd seen the look of pure joy on the guy's face in the video last night, and I wanted to feel Carla's balls bouncing off mine as she trained me to take her big dick.

She hopped up on the kitchen counter and spread her legs. "Come here baby," she said. "Time for you to get my girl cock ready."

I devoured her cock, licking and sucking her balls till she was again rock hard. I looked up as Carla unbuttoned her bra, letting her beautiful breasts free.

"Do you want to suck my nipples, sweetie?" she asked.

She didn't have to ask twice.

"Bite it baby, but not too hard," she insisted. I was stroking her cock as I gently nibbled her nipple, and I felt a gush of precum as I roughly attacked her breast.

"Rub that precum up and down my shaft; that's the only lube you are gonna get," she said.

Hopping down off the counter, she roughly pushed me against the cabinets and bent me over the counter top. She spread my ass cheeks and I felt her tongue against my opening. Within seconds, her tonguing of my ass had me weak in the knees.

"You like that don't you, you little slut?" she asked.

"It feels amazing," I moaned.

"What do you want now, honey?" she asked, as she gave my ass a firm swat with her hand.

"I want your cock, Carla. I want you to fuck my virgin ass," I whimpered.

"That's a good little bitch. I knew I could make you beg for it," she laughed.

She straightened up and I felt her lean forward, her massive cockhead resting right against my wet hole.

"Put your hands behind your back, baby," she ordered as she literally pinned me against the counter. She grabbed the dishrag and stuffed it in my mouth, "Bite down on that slut and get ready for the ride of your life."

She pushed forward, grabbing my hips roughly and I felt the head of her spear force its way into my tight sphincter. The pain was unbearable, and if it weren't for the gag in my mouth, I'd have screamed bloody murder. I knew it was going to hurt, but this was just too much.

She kept on the pressure, spitting on her cock as inch after inch of her huge rod ripped into my ass, penetrating deeper and deeper into my bowels. Pinned against the counter, I had nowhere to run, nowhere to hide; my ass submitting to her onslaught as the torture continued. I was sure I was going to pass out from the pain.

"Feels like your ass is literally on fire, doesn't it baby?" she moaned. "God, you are so fucking tight. I'm halfway home."

She took hold of my hands, pulling them backwards to keep me completely at her mercy even while she used the leverage to penetrate me more deeply.

"Oh you little slut," she giggled. "Your ass says no, but your cock is dripping like a faucet. Your seed is running down the kitchen cabinet as my cock milks your tight little hole."

At long last, I felt her balls bounce against mine. "I'm fully home, bitch," she muttered. "How does it feel having your new girlfriend buried ball deep in your little cherry ass?"

The fire was starting to subside, and while I was still incredibly uncomfortable, I felt the worst was over.

I spit the towel from my mouth, and moaned, "I think you are ripping me in two."

"Don't worry baby, you'll start to enjoy it very soon." With that, she grabbed my hips again and started to withdraw. Slowly at first, she began sawing in and out of my stretched hole, fucking my ass with her throbbing boner.

As she loosened me up, she started fucking me faster and with deeper strokes.

As the pain subsided more, I started to push back against her, getting into the rhythm.

"My little slut likes getting fucked in the ass, don't you?" she giggled.

"Yes, Mistress," I moaned. "Fuck my ass with your huge cock. Breed my virgin hole."

For the next 15 minutes she pounded my ass with no mercy. Fucking me like a wild animal in heat. My cock leaked non-stop as she rubbed against my prostate, filling me over and over with her full length. I wasn't going to be able to walk right for a month after this.

"Oh baby, I'm gonna fill your tight ass with my spunk," she cooed. With one final deep thrust, she collapsed onto my back. I could feel her pert breasts and glass-cutter nipples on my back as her monster erupted deep inside me. Her full weight on my back, she spasmed several times as blast after blast of hot cream filled my hole. The feeling was outrageous, and it pushed me over the edge, my cock exploding without even being touched as I shot my wad against her kitchen cabinets.

"Did you like getting your ass fucked and filled by a girl?"

"God yes; you can take my ass anytime, anywhere," I replied.

"That's the plan," she giggled as she slowly stood back up and started to withdraw, leaving me feeling so empty. I could feel the cool air from the ceiling fan blowing up my gaping hole as Carla's molten lava slowly dripped down my legs.

"Look at the huge mess you made on my cabinets, you dirty little slut," Carla snickered. "Get down on your knees and clean that up."

I was 100% under her spell and followed her command without hesitation, licking the dripping cum up like a hungry dog.

"Oh, you are a nasty little pig, aren't you Scotty?" she said. "I bet you'd do almost anything to please me, wouldn't you my little fucktoy?"

It was true; I was willing to be her submissive little puppet to have the pleasure of her big cock. In the last 24 hours, my whole outlook on sex had changed 180 degrees. She looked so beautiful towering over me, her big, swinging dick hypnotizing me like a lovestruck teenager. I wanted Carla to be my girlfriend, but I wanted Carla to treat me like her bitch-in-heat.

"Yes Mam," I complied.

"I am so happy at how this little relationship is progressing," she giggled as she smacked my cheek with her heavy tool. "I could only have dreamed you wouldn't be repulsed by my secret. So much better that you are also a submissive little slut with a tight ass and a hunger for cum."

"Sounds about right," I chuckled as I milked the last couple of drops of hot cum from her slowly deflating cock.

"If you think you can get it up again, I'd love for you to fuck my ass next," she teased as she turned and walked toward the bedroom.

Watching her beautiful butt sway so enticingly, I felt my cock start to harden. A huge smile spread across my face as I replied, "I'm right behind you baby."

"Literally I hope," she laughed.

We fucked like bunnies the rest of the night. When I woke up in the morning, my body ached like I'd just run a marathon (although my ass was never this sore after a long run). We showered together, and I couldn't resist blowing her in the shower. Seeing Carla naked, her stunning beauty combined with that big powerful cock dangling between her legs was the dream I never knew I had come true. Her sweet load was the best breakfast ever.

"Scotty, I think this is the beginning of a beautiful friendship," she quipped, in her best Bogart impression, as I swallowed the first of what I hoped was to be many morning loads.

12
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
39 Comments
NikkiSiDeeNikkiSiDee3 months ago

Everyone should be so lucky to find a Beautiful hung Shemale! This is an exciting thrill-ride! An erotic narrative of just how exotic transexual sex can be. Great sexy read!

ShortyMacShortyMacabout 1 year ago

OMG That was one super hot story. Back in 2017 I met a transgender women named Summer. We were both at a homeless shelter and became friends. She had two roommates in her apartment at the shelter. All three of them were black and Summer’s other two roommates were real women. Once I got my apartment I invited the three of them over. Over the next four years Summer and I both lost track of her roommates, but every Saturday night Summer would come over and I’d cook dinner and then we watched a movie. We never did anything sexual but we did talk about sex. I told her I would love to be with her. Her excuse was that she was a size queen. Then in late July 2021 Summer dropped out of sight. Finally in November she showed up at my door around midnight. She was homeless again and hungry. I fixed her something to eat and when she was done she was still hungry so I fixed her more. After she was full we were sitting on my couch talking and she had a strange look in her eye. She looked at me and said, “Do you want to touch it?”

Four + years I waited to hear those words from her. “Hell Yes!” I said. She undid the string holding up her sweatpants and pulled them down. I couldn’t believe what I saw. Summer was HUNG and ROCK HARD already at least 10 inches and a girth as big as my wrist. I dropped down and took her in my mouth. No mater how hard I tried I could only get just over half of her in my mouth. I sucked her for about 20 minutes then ask her to fuck me. We tried several different positions and she was just too big. So I went back to sucking her. I could at least suck her off. An hour later she still hadn’t cum. My jaw felt like it was going to dislocate. We finally stopped and I gave her the bed and I slept in my recliner. Next morning she took a shower and came into the living room naked and again rock hard. I tried for another hour to get her off no cum. I found out that night why. I caught her smoking Meth. If a guy smokes Meth it’s like taking Viagra, but it’s almost impossible to cum. I had to ask her to leave because if she was caught smoking Meth in my apartment I could get evicted and lose my rental subsidy. She freaked out telling me if she leaves I’ll never see her again. I haven’t seen her since.

ColonelinguistColonelinguistabout 1 year ago

Carla: absolutely gorgeous, and a huge cock to top it off!! What man could possibly resist, straight or gay?

tslover1963tslover1963over 1 year ago

Beautiful story, hope there are more chapters to cum, he’s living the life I fantasize about, oh, to be Scotty

PervyHusbandPervyHusbandover 1 year ago

I’d love to find myself a sexy Carla!! ❤️

Show More
Share this Story

Similar Stories

My New GF has a Dick And I love every last inch of it.in Transgender & Crossdressers
My New Trainer Workouts will never be quite the same.in Transgender & Crossdressers
The Happiest of Endings A massage with a big, hard surprise.in Transgender & Crossdressers
Shemale Surprise A married man is seduced and taken by a friend of his wife's.in Transgender & Crossdressers
My Transgender Neighbor Mike falls for his blonde transgender neighbor, Caroline.in Transgender & Crossdressers
More Stories