My name is Shaye and I’m a 27 year old pre-op transsexual. This is the story of my only sexual encounter with another shemale, which turned out to be one of the most intense sexual experiences of my life.
I first started speaking to Aimee about two years ago on an adult chat site. We had some cyber fun for a few months, jerking off on cam and generally having a good time. Eventually, Aimee asked me if I wanted to go around to her place for some real fun. I didn’t need to think about it and I arranged to go to her house a week later.
It took me two hours or so to drive to her house. More than once during the drive, my cock became semi-erect at the thought of spending the night with Aimee. I had seen her do wild things on cam, things that got me hard, jerking and shooting a creamy load in a matter of minutes on several occasions. My cock began to harden again at the memories and fantasies floating through my mind, and a slight bulge began to form between my legs, propping up my black cocktail dress. I purposefully hadn’t cum for four days, and I needed something.
With some difficulty, I pushed thought of Aimee and the night ahead out of my mind. The drive was almost at an end and I didn’t want to arrive at Aimee’s house with a fully erect cock. As fun as the thought was, I would probably attract some stares on the walk to the door. Eventually, the concentration required to navigate unknown streets was distraction enough to allow my burning desire to settle, and I arrived at Aimee’s at about 6.30, my cock soft and appropriate.
I stepped out of the car and onto the pavement, my tight dress sliding up my thighs as I did so. My heels clipped along the stone as I walked. I wore my long hair down, which blew about my face and shoulders. I reached Aimee’s door and tapped the glass four times, my stomach suddenly churning with nerves and anxiety.
I heard light footsteps hurrying towards the door and saw a blurry shape emerge behind the glass. The door opened, and I swallowed. Aimee was beautiful. She stood around 5 and a half ft and had long, jet black ebony hair which she also wore down. Her skin had a deep, olive tan to it that almost seemed almost to glow. She looked to be of Latin descent, but I never found out for sure. She wore a crop top which showed off her amazingly toned stomach. Her long, perfectly shaped legs emerged from some fabulously short hot-pants.
“Come in,” she said. Her voice was like honey and seemed to melt as it hit my ears. I followed her inside as she walked down the hall, her round and shapely ass wiggling as she walked. I felt a slight stirring at the thought of holding that ass in my hands.
“Did you find the place okay?” Aimee asked.
“Yeah, it was fine,” I said, as we entered her living room. The sofa was a big, soft looking, creamy leather number. On the table in the middle of the room was a bottle of red wine and two glasses.
“That’s good. We don’t want you too tired do we?” she said with a wink. “Have a seat”.
I sat down and sank into the enormous sofa. I crossed one leg over the other and sat with my hands resting on my thigh.
“Would you like some wine?” Aimee asked.
“I would,” I said, hoping it would calm my nerves slightly.
Aimee stood right in front on me facing the table. She slowly bent over in front of me to pick up the wine, giving me a fantastic view of her perfect ass. The hot-pants hugged her bubble ass cheeks tightly and formed nicely along her ass crack. As she bent lower, her pink thong slipped above the waist line of her shorts. My own thong felt like it was beginning to shrink as I stared at the wonderful thing in front of me. I adjusted the position of my legs to try and conceal the soon-to-be bulge that would appear between my legs.
She yanked the cork out of the bottle, giving an exaggerated orgasmic moan as she did, and began to fill the two glasses.
“There you are,” Aimee said, handing the full glass to me. She sat close to me on the sofa. She smelled as amazing as she looked. I took a sip of wine as Aimee rested a soft hand on my knee.
“You seem nervous?” she phrased it as a question.
“I am a bit,” I admitted.
“Me too,” she said, taking a gulp of wine and giving my knee a reassuring squeeze. “But I’m still going to give you an incredible night.”
She started to move her hand up the inside of my thigh. The smooth, sensual feel of her caress sent shivers through me. Aimee seemed to sense this and squeezed my thigh harder and she slid her hand along my thigh and under the hem of my dress. I squirmed as her hand inched slowly towards my hardening cock. With her other hand she grabbed my chin and turned my face towards hers. Her eyes were deep and dark. Her black hair framed her delicate face perfectly. She looked at me with the most lust filled expression I have ever seen. Her lips were full, shiny and completely irresistible. I leant towards her slowly, feeling her warm breath bounce off my face.
“You’re beautiful,” I said.
“So are you.”
I lightly kissed her lips, so soft we barely seemed to touch. A spark went though me, and Aimee let out a low sigh. She moved towards me and kissed me deeply. Her tongue eased its way into my mouth and I tasted the warming taste of red wine on her. A moan escaped my lips. Frustratingly, Aimee removed her hand from my thigh, which was centimetres away from my now fully erect cock. She stopped kissing me and took the half empty glass of wine from my hand and placed it on the table along with her own. She sat back and put her arm around my waist, gently pulling me around towards her.
“Get on top of me,” she said.
I knelt on the sofa, the bulge of my cock clearly visible through my black dress. Aimee had a glance at it and smiled. I placed a knee either side of Aimee’s thighs and slowly lowered my ass into her lap. My dress sliding scandalously high up my thighs, drawing even more attention to the painful hard-on concealed beneath. I put my hands around Aimee’s neck and moved in to begin kissing her properly. As I leant forward, my own hard cock came into contact with her hardened cock. Even though the fabric of my dress and the denim of her shorts it felt substantial.
“Big girl,” I said
“Honey, wait until it’s inside you,” Aimee said with a smile. My cock twitched at the thought as I buried by tongue deep in her mouth. I frantically ran my hands through her soft hair as she moved her hands up the back of my thighs and under my dress. She grabbed my round ass with both hands and began to squeeze the cheeks. I slowly started to dry hump her, rubbing my cock against hers through our clothes. This alone had an incredible feeling of intimacy about it, and I knew that this was going to be a night to remember.
Aimee worked her hands up to the elastic of my thong and began to slide it down. She had exposed about half of my ass when she decided to grip it tightly in her hands and rip it apart.
“Mmmhmm...” I moaned into her mouth as my body jolted against the force of her rip. She flung the thong, which skidded across the coffee table and landed on the floor the other side. The feel of the cool air against my hard cock was nice. Amy began to unzip my dress from the back. I sat up for a second to give her easier access. When she was done, I let the dress slip from my shoulders and let my breasts out into the room. Aimee instantly sat up and took my left breast in her mouth. She sucked and licked and slurped at my nipple. I set to work removing her top. She lifted her arms over her head and allowed me to easily slip the top off. She also chose not to wear a bra. She sat back on the sofa, giving me my first proper look at her body. She was incredible. Her olive tan shone in the lamp light, the only exception were the tan lines around her breasts, which drew perfect attention to them. They were large, but not overly big, with two perfect brown nipples. Her hair was wild about her head where I’d tangled it, making her even sexier. Her lips were parted in a half smile of satisfaction and lust, her dark eyes looking up at me as she breathed heavily.
I unclasped the button of her shorts and slowly slid the zip down. Her grin widened as she lifted her ass off the sofa and began to slip her shorts down her long, slender legs. The head of her hard cock poked above the top of her pink thong, a drop of pre-cum on the tip. I rubbed the hole of her cock with my middle finger, smearing her bulbous cock head with her pre-cum. Aimee closed her eyes and sensually licked her lips.
“Let me taste it, Shaye,” she cooed. I lifted my finger to her mouth and ran it around her lips. She opened her mouth and sucked my finger, moaning as she did. “Shall we take this upstairs?”
“God, yes,” I said, leaning in to kiss those perfect, wet lips again. I couldn’t get enough of those lips and the way she kissed. Firm, but gentle. Filled with passion and desire, but not greedy and sloppy. Just nice.
She gently pushed me away and I stood up. My dress was bunched around my waist, the cock obscenely bulging through it and my tits out. Aimee stood up, her cock becoming even more exposed as she straightened. It had to be seven inches, possibly eight; and quite thick. That thing was going to make me squeal, I thought.
She took my hand and led me upstairs. Her ass as she walked up the stairs was making my cock even harder. The cheeks were perfect. Rounded, bubble-butt style ass cheeks. I spanked one of the cheeks. Aimee let out a squealing, giggling scream and wiggled her ass at me. We entered the room at the top of the stairs.
Her bedroom was enormous, and had a king size, four post bed in the middle of the room which looked to be made of solid oak. She had lit candles all over the room and there was a dim red lamp lighting one corner. She put her hands around the small of my back and pulled me towards her.
“Let’s have some fun,” she whispered in my ear. She lightly sucked on my earlobe and worked my crumpled dress down my legs. I stepped out of it and stepped towards her. My now naked cock brushed up against her thong and we kissed. I caressed down her back and slipped my hands under her panties, feeling her ass in my fingers for the first time. I squeezed and kneaded the soft flesh, revelling the sensation; the smoothness, the softness. I ran a finger down the crack of her ass. My finger found the rough, fleshy mound of her ass hole and I began to circle it gently. Not trying to penetrate, just lightly circling.
Aimee eased her hand slowly down my stomach and over my pubic bone, to my achingly hard cock. She took it in her palm and gave it a light squeeze.
“Mmmmmmm,” I moaned, and began to grind my cock into her palm. She took the hint and began to slowly rub it. I took her thong in my hands and decided to go for a little pay back and ripped it clean off. She laughed, and pushed me roughly onto the bed. For the first time, I saw her cock in all its glory. It was between 7 and 8 inches, beautifully shaped and very thick. It was the perfect contrast to her curvy, feminine body and face. Her wide hips and small waist almost highlighted by the hard cock.
I lay on the bed with my legs apart, my cock throbbing in time with my pulse as she crawled up the bed towards me. She crawled between my legs and suspended her body over mine. She lowered her face slowly and kissed me, sucking my tongue as it entered her mouth. At the start of the kiss, she kept her ass in the air, but now she slowly lowered her crotch on top of mine. Our naked, hard, swollen cocks touched for the first time. We ground our hips, our cocks sliding together. Our pre-cum slurped together as she writhed and slithered around on top of me, her breasts pressing against my own. My hands clawed greedily at her as I tried to caress every part of her at once. Her skin was delicious to the touch; perfectly smooth and wonderfully soft.
We kissed and devoured each other in that way for about ten minutes before Aimee knelt on the bed. She crawled to the bedside cabinet, giving a wonderful view of her ass as she did. She took a bottle of lubricant from the drawer. She clicked open the lid and squeezed a dollop onto her middle two fingers. She was kneeling at the head of the bead, her cock jutting out from her body. She tensed the muscles in it, making her cock jump up and down.
“Come to me, honey,” she said. I crawled towards her and knelt in front of her, putting my arms around her neck. I shifted my body towards her and our cocks touched again. I kissed her deeply. She moved her hand between my legs and under my balls. “Are you ready to have something inside you?”
I nodded my approval. She pressed her middle fingers against my ass hole. The cold sensation of the lube made me jump a bit. She slowly began to circle the middle finger around my hole, increasing the pressure. The second soon joined it and she increased the pressure against my tight hole.
“Let me in baby,” she whispered.
She pushed harder and I relaxed my ass. Her fingers broke through the sphincter with a heavenly pop. I let out a long sigh as her fingers slipped up to the first knuckle and beyond.
“Ohhhhh......” I let out a long moan as her second knuckle disappeared inside.
She began to kiss me. Gentle yet firmly, her tongue dancing around my lips. As she kissed me, she suddenly curled her fingers forward, causing them both to come into direct contact with my prostate.
“UNGH!” I tightened my grip around her back as she began to massage my rapidly swelling spot. “Fuck....That’s it.” She expertly ran her fingers along the length of my prostate, keeping firm pressure directly on it all the time. My cock began to leak pre-cum, which was rubbing all over Aimee’s cock. The sight drove me wild and I began to practically suck her face off as her miraculous fingers pumped inside me. She pressed her thumb firmly into my swollen perineum, and began working my prostate from the outside as well. I moaned deep in my throat; a guttural, animalistic sound as my cock and ass spasmed around Aimee’s fingers.
“How does that feel?” she asked.
“Fu....Fucking....unbelievable!” I replied, gasping uncontrollably. “Put a third in.”
The third finger slipped in easily. My cock was streaming pre-cum and was involuntarily spasming as Aimee finger fucked me. I could feel an orgasm approaching. It was a long way off, but it was definitely on its way. I could tell it was going to be mind-blowing. My whole lower body was filling with pleasure. I could feel it in my cock; my ass and deep in the pit of my stomach. I took Aimee’s thick cock in my hand. I could feel her pulse through it. I began to jerk it, using mine and her pre-cum as lube. Grabbing her cock in my hand seemed to take me ten steps closer to orgasm in an instant. Her three fingers deep in my ass, her breasts pressed against mine, her eager tongue flicking around my mouth; and now the feeling of her pulsing cock in my palm was too much to handle. My ass began to tighten around her fingers and my prostate began to harden. I was about to cum.
Aimee stopped working her fingers. I could barely contain my disappointment. Neither could my cock, for that matter. I looked at it and saw a virtual puddle of pre-cum on Aimee’s sheets. The white creamy flow of cum wasn’t far behind.
“Easy there, honey,” she said, slipping her magical fingers from my ass. “It felt like you were about to blow your load all over my bed there?”
“I was getting close,” I admitted. “Your fingers are incredible.”
She gave me a soft kiss on the lips. “That’s nothing,” she said. “You’re about to feel my cock inside you.”
Aimee gently pushed me down onto the big, soft bed so I lay on my back. I took the bottle of lube and squeezed it into my palms and rubbed them together until they were suitably slick and wet. I took her cock in both of my hands (it was big enough to do so easily), and I began to slowly massage the lotion over it.
“Mmmmmmmm,” she purred. She began to rock her hips in time with my hands until we felt that she was ready.
I lifted my legs over my head and spread them as wide as I could, exposing my ass completely to her. She held her cock in her right hand and gently pushed the head against my sphincter. She stopped there for a minute, allowing me to get used to her. We kissed and groped and stroked each others’ bodies. Eventually she began easing her weight forward, encouraging my ass to accept her.
“Relax, baby,” she said. I took a deep breath and let it out slowly. As I did, Aimee pushed more pressure onto my ass and the tip of her substantial head began to slip inside me, a bit quicker than I had anticipated. I gasped. “Sssshhhhhh.....”
We waited another minute or two for me to get used to her before she started to gently rock her weight back and forth. Each time she rocked forward, her cock would slowly creep into me. She was stretching my ass further than it had ever been stretched before. While it was painful, the pleasure was immense as well. When she was about two inches inside, her cock collided with my swollen prostate.
“Mmmmpphhh...” I looked down at my cock. The concentration required to get Aimee inside me had left it soft. As soon as she hit my prostate, my cock began to harden. It took about ten seconds to go from completely flaccid to spring board hard, complete with a globule of pre-cum dripping down the tip.
“Ram it in me,” I said.
She looked at me grinning and thrusted herself into me. I let out a sharp hiss of air which I expelled in a long, deep moan. I’d never taken anything as big as Aimee, and the feel of her stretching my ass was better than anything I’d ever felt. My cock was ready to explode and I needed release.
“Fuck me, baby,” I said.
She kissed me and began to slowly thrust herself in and out of me. Each time she thrust, her cock would brush against my hardened, sensitive prostate which would cause my cock to spasm involuntarily. Aimee had been fucking me for all of ten seconds, and I could already feel a big orgasm building deep in my ass. Aimee took my breast in her hand, and squeezed my nipple between her thumb and forefinger.
“Faster,” I said.
She began to quicken her thrusting. Now she was pulling back until her cock was almost completely out of me. I could feel the base of her head slipping out of my ass before she rammed it all the way inside. I gripped her ass and pulled her into me, encouraging her to fuck me harder. The head of the bed was crashing against the wall and the whole bed creaked and groaned around us. The pleasure in my ass was beginning to build to an almost unbearable level. I could feel a substantial pool of pre-cum collecting on my stomach. Aimee kissed me, her breasts pushing against mine as she fucked me faster and faster. I knew I wouldn’t be able to hold back for much longer.
“Your....gonna....make.....me cum!” I gasped between thrusts. Her cock hitting my prostate was driving me closer and closer. My ass was beginning to spasm around her.
“Don’t hold it back,” she moaned. “I’m close too, and I want to shoot deep in your ass.”
She fucked me faster still. Her sweaty, clammy, perfect body writhed on top of me. I curled my legs right up to my chest and linked my ankles around her back, allowing her to get deeper into me. The altered angle of my body meant her cock was now pounding almost directly into my prostate. Almost instantly, I was on the edge of orgasm.
“Jesus.....I’m gonna blow. Keep it there”. The pleasure began to build and build; I wasn’t even touching my cock. My ass began to clench with incredible force around Aimee’s thrusting cock as my orgasm neared. My cock got harder and harder as I approached the point of no return.
“Ah....ah....ah.....Fuck me, Aimee!” I wrapped my arms around her shoulders and pulled her tight against me and squeezed her mercilessly with my legs. My ass clenched harder around Aimee as I reached the peak of my orgasm, that point just before cum starts to flow, where everything is locked in a vice like contraction and the only thought in your head is the immense, unbearable pleasure surging through your body.
I let out a long, guttural, grunting moan as my ass spasmed rhythmically around Aimee.
I felt my cock begin to buck and dance as cum erupted from it. It shot up to my breasts and beyond, covering my entire body in a white sticky sheen. My whole body convulsed and flailed under Aimee as wave after wave of orgasmic pleasure shot through me. Each time Aimee thrust into me, she would force out another spurt.
“Your ass clenching around me was too much baby, I’m about to cum”
She quickened her thrusting, which delighted me as my orgasm was more or less still going on and the feeling of her sliding in and out was eye rolling. I clenched my ass, making it tighter. She picked up the speed and I could feel her cock hardening and increasing in girth inside me.
“Shoot inside me,” I said.
Her cock seemed to get even harder as her whole body tensed.
“MMMMPPPHHHH!” she moaned. Her cock started to twitch inside me and I felt the warm, squelchy feeling of her cum filling my ass. A small amount dribbled down my ass and got on the sheets. Aimee let out a final moan and collapsed on top of me, her cock still giving the occasional twitch in my still spasming ass. She looked at me with her dark, beautiful eyes. Her hair was clinging to her sweaty forehead and she was breathing heavily.
“That was incredible,” I said.
She grinned at me and lowered her head to kiss me softly, deeply and with more passion that I’ve ever known. Her cock still deep in my ass, slowly softening while we kissed.
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