Our First Shemale Erotic Story!

"Damn another Valentine's day spent alone," I mutter crushing another beer can and tossing it in the corner. This was the sixth consecutive Valentine's Day I had spent right here in my shitty apartment slumped over in my recliner getting wasted on cheap ass beer. The problem wasn't getting the girl, it was keeping the girl and I'll be damned if every time I had a steady relationship we never made it until Valentine's Day. I was cursed I tell you cursed with the St. Valentine's Day Curse. Janelle, my most recent relationship broke up with me two, count em two fucking days before Valentine's Day! Cursed I tell you I'm cursed!

It was a horrible holiday anyway, ruined by unrealistic expectations and the media, not only that but this particular Valentine's Day it was raining like cats and dogs outside and a thunderstorm was brewing.

"Damn it!" I said turning off the TV and dropping the remote nothing on TV but sappy ass chick flicks and romance movie marathons. I grabbed my keys off the counter and decided to go for a drive to clear my head and escape my loneliness. I was just a little buzzed but still plenty lucid enough to drive. It was around eleven something at night as I cruised the streets downtown, the few people I saw still on the streets were mostly couples running hand in hand to their cars or homes to get out of the rain, "The curse strikes again," just serving to remind me that I was alone.

I turned down Main Street and saw all the storefronts advertising their holiday specials with posters of couples kissing and holding each other. The sight made me sick to my stomach with loneliness. I'll be glad when morning comes and this god-forsaken day ends. I drove around town for a while with images and constant reminders of my loneliness at every turn. The café were Janelle and I first met, the place beside the light pole where we first kissed, god it was downright sickening. I was beginning to think another lonely Valentine's Day with Mr. Checkers, my cat or Janelle's cat I should say was better than this tour of torture. I turned down the street that would take me back to my apartment and my empty bed.

I felt like the most miserable guy in the world as I drove down the backside of main street. Then I saw someone that looked like they were almost as miserable as I felt, they were huddled under a jacket at the end of the corner. As I got closer, I could make out a female form. I slowed down to get a better look. She was a tall blonde-haired woman with sexy legs wearing a short skirt and tight top with high-heeled fuck-me pumps on. I knew immediately she had to be a prostitute or a woman caught in the rain on the way to her boyfriend's for a very hot night. Either way I decided to stop.

I slowed the car down beside her and rolled down the window

"Can I give you a ride somewhere?" I asked as she turned and looked at me with the most beautiful deep blue eyes I had ever seen. Her long wheat colored curls fell limply off her shoulders heavy with rain.

"Listen I'm off the clock and I just want to get out of the rain."

"That's fine with me," I said confirming my earlier assumption, she looked at me hesitantly and then looked down the street at the pouring rain.

"Okay but I'm serious no funny stuff, my feet hurt and I want to get out of the rain."

I nodded and she circled in front of the car, as she walked in front of the headlights I saw she had a nice ass to match those long shapely legs. She opened the door and got in.

"Where to?" I asked as I pulled off.

"The starlight motel."

I raised an eyebrow at her.

"Like I'd tell you were I live," she said. "No offense you look nice enough but I see enough crazy fucks in my line of work to know not to trust people based on just their faces."

"Point taken," I said.

She took off her pumps to rub her beautifully pedicured feet; it was a long drive to the motel.

We drove in relative silence as some sappy love song droned on the radio and she continued to rub her feet.

"God I hate Valentine's Day!" she exclaimed as the song entered its chorus.

"You and me both," I said, "say umm what's your name anyway?"

She stopped rubbing her feet and looked at me with a smile "Mai, Mai Valentine."

"Bullshit!" It was so ironic I had to laugh, "You gotta be kiddin me," I said

"Afraid not," she said as the she tucked her damp curls behind one ear and smirked at me.

I thought to myself "yep, the curse is just fucking with me now."

"Ok Mai Valentine," I said sarcastically "I know why I hate this card corporation sponsored love-fest why do you?"

"Don't get me wrong I get more money on Valentine's Day sometimes than I get on any other day of the year. But I hate always ending up alone at the end of the day or fucked dry by some prick of a guy who only paid me extra just so I'd spend Valentine's Day with him so he didn't feel like a loser."

"Yeah I get it," I said, "My name's Cal by the way." I hoped my face wasn't too red because I easily could have been one of those guys on any other Valentine's day.

"So why do you hate this wonderful day Mr. Cynical?" She asked.

"Because I'm cursed," I said

"Cursed?"

"Yep," I said explaining the whole St. Valentine's Day disasters of the past.

I finished my pathetically sad tale just as we pulled into the Starlight motel parking lot.

"Poor Cal" she said patting my thigh before getting out of the car; she turned to close the door but hesitated for a few moments.

"Ah listen Cal I don't normally do this, but come on up and we can do whatever you want half-price, the good Samaritan discount." she said leaning on the car door looking at me with those gorgeous blue eyes.

I hesitated before answering, the sex starved part of my brain screamed at me to say yes.

"I would love to but no," I said "besides why would you want to spent another Valentine's Day getting fucked by some stranger?"

"Well at least come up for some drinks, your sad story has got me feeling sorry for you." She said with a smile.

"Thanks but no thanks." I said

"Why spend another Valentine's Day alone with Mr. Checkers?" She said.

With those words, I finally relented and circled around the motel to look for a place to park.

The room was about what you'd expect from a place called the Starlight motel but it wasn't too bad, kind of cozy if you just wanted a place to crash.

I sat on the bed while Mai made us some drinks. After we each downed a few Mai told me some of the most outrageous things she had seen in her line of work and a bit about some of the johns she had met, "You'd be surprised what some people are into these days." She said. "You ever heard of The Burmese Butterfly?"

"No, Should I?"

"Good", she said chuckling to herself. "Do yourself a favor and don't Google it."

I could tell I was well on my way to drunk by the sixth drink and Mai noticed too, she was tipsy but I was wasted.

"I think you have had enough Cal" she said giggling.

"Nonsense, I can walk in a straight line and everything," of course I stumbled taking my first step and tumbled right into Mai on the third.

My head fell into the nape of her neck. Her scent, the scent of lavender from her hair filled my nostrils and made my drunken mind swim with warmth and pleasure. I felt her large breasts pressed against my chest.

"Upsy-daisy Cal" she said lifting me to my feet, my head lulled on her shoulder still breathing in her wonderful sent.

"You smell nice," I breathed heavily into her neck.

"I know Cal," she responded sweetly.

I raised my head to look at her angelic face and mesmerizing blue eyes. Her bubble gum pink lip gloss covered lips looked so good I just had to taste them. I kissed her on the lips drawing those full pouty lips into my mouth and suckling on them. Slowly my tongue worked its way into her mouth her tongue welcoming mine in a swirling tongue massage. Our tongues danced and darted around each other's mouths as we each began to discard our clothes as fast as we could between kisses.

She had removed her top revealing her ample bra laden chest and I was naked from the waist up. I leaned in for another madly passionate kiss as she unzipped my pants. I dropped my pants and stepped forward to remove her skirt. I wrapped my arms around her, slid my hands into her panties from behind, and squeezed her firm ass in each hand. She moaned seductively in my ear. I worked my hands back up her backside and undid her bra. The bra fell away revealing small hard pink nubs of her nipples and large breasts lightly dusted with freckles. I took one of the hard pink nubs in my mouth and sucked gently. Mai shuddered and pressed my head into her chest with surprisingly strong hands before pulling my face up to kiss her again. I felt her large breasts pressed against my body, her hard nipples rubbing against me as we fought to kiss deeper as if we were trying to devour each other.

I went in for one more passionate kiss before plunging my hand into the front of her panties...

I grasped something that wasn't all that unfamiliar but unexpected, it took a few moments for my alcohol addled mind to comprehend what was happening. Then realization hit me like a bucket of ice water. I stumbled back and tripped over the chair, I landed on my ass and hit my head on the wall. My head reeled for a moment from the pain. Then I looked up at her, it was so sad I was close to tears.

"It was stupid of me to think anything good could come of this abomination of a holiday" I laughed drunkenly, actually it was more of a sob really, as the full weight of my life hit me.

My beautiful Janelle gone and now my angel, my only ray of light on this day and she turns out be just another cruel trick of the cosmos on this garish and hellish day.

She was a.... HE! or a She I don't know, all I know is that whatever Mai is it was a horrible joke and I was the punch line.

"No, damn it NO!" I screamed. "Why? I just thought that just maybe this would be at least one Valentine's Day not filled with pain and bad memories," I sobbed.

"I'm so sorry Cal, I thought you knew" said Mai stepping closer to me.

"You're just another part of the curse here to mock me," I said genuinely crying now.

"God! How stupid of me, a girl with perfect long shapely legs, a rockin body and killer tits.... Yeah and a dick bigger than mine;" I announced to the universe, "You really got me this time!"

I continued to sob in the corner for minutes on end with Mai looking on in pity. After a while Mai sat next to me against the wall, pulled me close and laid my head on her shoulder. I wanted to resist, to leave but part of me just felt broken and wanted to be comforted.

"I'm sorry Cal but everything will be fine," she said in a soothing voice stroking my hair. Neither of us said anything for a long while, I just lay there with my head on Mai's shoulder as she stroked my hair.

I lifted my head and looked at her or was it him? Oh whatever I didn't care, I just needed to be close to someone. I kissed Mai on the lips.

"Wait Cal...," she said pulling away from me and looking at me. Her big blue eyes looked genuinely concerned.

I said nothing I just went back in for another kiss and she hesitated before finally reciprocating, we kissed in blissful silence for what seemed like an eternity. The only sounds in the room were Mai's husky breathing and our wet kissing. Then Mai pushed me back against the wall. She looked at me with those sexy blue eyes then slid off my pants and boxers exposing my now semi erect dick. She looked at it lovingly and then she wrapped her warm hand around my dick. The cold metal of her rings making my dick stir. The sensation caused me to take a sharp intake of air.

Then she enveloped me in her hot wet mouth, drawing the head into her mouth and swirling around the tip before licking long and slowly up the base. Her eyes never left mine as she sank her head down drawing in my full length in one motion. Slowly rising and plunging back down my shaft again. Those deep blue eyes were steadily seducing me making me forget the surprise that waited between her legs, at that moment she was a sex goddess and I was hopelessly spellbound.

I lay my head back against the wall and closed my eyes and enjoyed the rhythmic sucking and slurping noises and the professional treatment my dick was getting. Her mouth was so good I could have died at that moment and never been happier. I felt the cum building in the base of my cock, moments from erupting, I reached out and stopped her, I wanted whatever this was to last as long as possible. She took my hand in hers and pulled me up. She crawled onto the bed on her hands and knees and left me there gawking at her shapely round ass. She reached behind her and pulled her panties down. I watched her as she sucked on three fingers and rubbed the saliva into her exposed asshole. The sight of her massaging her spittle into her ass and moaning softly was so erotic and looked so inviting, I didn't care that dangling below her were a pair of balls and a hard dick, I didn't care what she was anymore, in fact all I knew is that I wanted her.

I moved her hand away leaned forward and sucked her fingers dry. I positioned my cock against her asshole rubbing my pre-cum in with her spittle before slowly pushing it into her ass. My dick felt like it was in heaven as it slipped past her sphincter, her spit and my cum making the perfect lube. I slowly pushed in deep as I could go enjoying the hot fleshy cloud like sensation. The tightness around my dick as I thrust in and out of her hot ass was intoxicating. I was driven on by her building moans as I fucked her ass harder and harder. She supported herself on her forearm and pumped her cock with her free hand as I pounded her ass. Her bowels were heavenly, her anal ring squeezing my cock and her soft insides milking my cock for all it was worth.

Just when I thought I was going to explode deep within her, I got my second wind. I grabbed her leg and I turned her over, put her long sexy legs over my shoulders and pulled her against me. I redoubled my efforts thrusting harder into her. I watched her face contort and moan in pleasure as I fucked her. Her hard dick twirled around in circular motions with each thrust I made. I felt my cum rising so I slowed to long full thrusts pulling almost out of her and then pushing myself back in again. I pulled out all the way to the very tip this time and rammed my dick back in sending jets of thick cum splashing deep into her bowels.

I watched her stroke herself furiously as my cock rapidly deflated inside her. She came sending cum of her own soaring into the air splashing on her chest and stomach. I crawled lazily onto the bed next to her both of us breathing wildly as we came down. I looked into her lust spent blue eyes and felt something akin to love just for an instant.

We lay there just holding each other and looking into each other's eyes for I don't know how long. I wanted to say something, anything, to apologize for earlier; to thank her for what just happened but no words came to my lips. My lips just opened and closed. She placed a finger to my lips and said "Shh, you don't have to say anything Cal;" with those words I was content to just gaze into those deep blue eyes as I ran my hand over her silky smooth body, tracing every curve with my fingers and occasionally nibbling at her succulent lips. Our touching and fondling continued until Mai started to grind her body against mine.

Mai used her hand to rub both of our cocks together. Feeling her hot dick flesh next to mine was intense and strange but more than anything it felt good! I felt her pre-cum run between our dicks. She pumped her long slender fingers over both our dicks.

I started to look down but she caught my chin in her left hand and whispered, "Just look at me and enjoy the sensation Cal." I nodded dumbly as if hypnotized and she kissed me again and again. Each time more lusty and passionate than the last until her cock spasmed and erupted coating both our dicks in her cum. She squeezed her softening, cum covered cock into mine. Her cum drenched fingers expertly making me cum soon after. With our dicks still pressed together between us we both drifted off into dreamy slumber.

RING! RING! RING!

I rolled over in bed to answer the phone. "Hello?" I said groggily into the receiver.

"Sir?" said the desk clerk's voice "We need you out of the room by 10 A.M.

"Huh?... ah yeah" I said hanging the phone up. I looked around the room but Mai was gone. I sat up on the bed and looked over at the spot where she had slept, remembering her. I got up to check the bathroom on the off chance she was in there, even though I knew in my heart she wasn't.

I got into the shower and turned on the water the maximum temperature of which could barely be called lukewarm but I let it wash over me as I thought about Mai. Another woman gone forever from my life but maybe Valentine's Day isn't all card corporations and gaudy bullshit. I thought to myself as I ran my hands through my hair and my dick twitched as I remembered the feel of Mai's cock against mine.

"What am I saying, of course it is, after all the part worth remembering technically happened after Valentine's Day didn't it?" I said to myself smiling as I turned off the shower.

The End.

Bill was not in a particularly good mood when he woke that morning. It was
Monday morning and he was waking up alone for the first time of what would
be at least a five day stretch. The love of his life, Sharon, had left the
day before for a full week business trip to some fitness convention. She
wasn't very happy about it either, but she had been convinced that it was
something that needed to be done to further her career as a fitness
trainer. He understood all of this but it meant nothing when he considered
he would be without her company for the entire week.

Not going to bed at night all snuggled up after another episode of the
hottest sex and waking up with either him holding her or her holding him or
some combination of both wrapped up together. The fact that she was a
pre-operative transsexual meant nothing, well, nothing beyond the fact that
he had come to love sucking cock, fucking a tight ass and having his fucked
in turn. He hadn't turned his back on conventional sex, as Sharon's sister
could attest. Her recent visit, during which she had pleaded with him to
father her ***** provided plenty of proof.

The first time they had met she had recently gone through the dissolution
of a very troubled marriage. Bill had shown her that it was possible for a
man to be honest and loving and above all else, sexy as hell. She had
succumbed to his youthful charm, although it appeared she had done the
seduction, and found redemption in his arms and bed. The second visit had
brought the plea to give her what she always wanted and after repeated
bouts of impassioned love making, she did indeed get pregnant, but was
still some six months away from motherhood.

He even had had some sexual adventures with Sharon's business partner, a
hugely muscled former competitive body builder who was a total gay bottom
who was only interested in masculine men. But none of that was going to do
him any good without his Sharon there to share it all with. He was due at
school, now that the regular semester had started and he had a job to do.
Not his usual lawn maintenance work, but a posing session for an art class.
The professor had spotted him in the gym and had asked if he would pose for
some studies by his beginning students.

His comment that Bill had the most finely detailed musculature he had seen
in at least thirty years was very flattering and had brought a big smile to
Sharon's face, as she had been largely responsible for the fine tuning that
had taken him to the next level. At least today, he wasn't going to have
to worry about nude posing, they were working on just torsos right now.
Bill was now slouch with a paper and pencil, but he had no illusions about
making a living as an artist. He was switching to become a certified
fitness trainer.

So after a light breakfast, he climbed into his battered pickup and drove
the 25 minutes to the campus. He reported to the studio room and met with
the professor.

"Mr. Cooper, thank you for coming. I won't say it will be easy, most
people finding remaining still for extended periods of time somewhat
difficult, so if you start to cramp up or feel uncomfortable, just let me
know. To start I'll ask you to sit so that the students get a three
quarter view of your torso. You'll be using the padded stool there."

Bill had worn a loose fitting long sleeved shirt to make getting it on and
off easier. The students began to filter in and take their places around
the room, basically chairs with easels in front. It was a mixed bag of
girls and guys, mostly younger but a few older students thrown in.