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The Surprise between Sasha’s Thighs

Derrick discovers his old crush isn’t what he expected, but she's still his crush regardless. . .
It was a sunny Friday afternoon as I sat at the dining room table of my apartment, behind my laptop with a bowl of dry Cheerios to my left and a glass of orange juice to my right, I typed away, working on my last paper of the week. You’d figure that after four years of college, I’d never want to write another paper again and you’d be right if the desire for a Master’s degree hadn’t called my name. Four years of hard work at Gwynedd-Mercy College earned me my Bachelor’s degree in Psychology, but to even get my foot on the Psychology field I'd need my Ph.D so after a summer break I entered Temple University to continue my education. Suddenly, the front door opened and my roommate Brian called out for me.

"Yo, Derrick!" he exclaimed, but lowered his tone at the sight of me in the dining room. "Oh sorry, D. I see you're working."

I smirked, continuing to type, "I can still talk."

"Okay, I got an invite to a party and was hoping you'd come with."

"Hmm, I don't know, Brian," I replied. "I know it's the weekend and all, but I'm just trying to chill tonight."

I can guarantee Brian had a sly smile on his face as he countered with, "Would you still just try to chill if Sasha was going to be there?"

Hearing the name Sasha forced my heart to skip a beat and my hands away from my computer.

I turned halfway around in my chair, "Sasha's going to be there?"

"Yup," Brian said with a laugh. "Not trying to chill now are you?"

"You know how I feel about her, man. Don't play with me," I told him deadpan.

"Trust me Derrick, I'm not. Hell, she's the one who invited us to the party. You know you want to see her, so how about it?"

I smirked, "Looks like we're going to a party tonight. Where's it at?"

"Club Onyx,"

"Cool, but I'm going for Sasha, man. I'm not trying to be out all night."

"I know . . . you’ve got work to do. If you want to leave early than get Sasha to give you a ride 'cause I'm getting wild tonight,"

I shook my head at friend, "A year removed from school and you're still a party animal."

Brian smiled, "A year removed from school and you're still crushing on the same chick."

"Whatever man," I said returning to my work as Brian went to his room.

Brian was right though. We were a year removed from college and I was still stuck on Sasha Smith. Sasha and I met when she came to Gwynedd my sophomore year. I'm won't say it was love at first sight, but it was something at first sight. Sasha was friendly and kind from the moment we met, so we became friends fast. When I wasn't with Brian (who was also my roommate in college) and my guy friends, I was with Sasha. Mostly, when Brian and my friends would drink and party in our dorm room. Being around such a beautiful woman it was impossible not to catch feelings for her. I liked Sasha though throughout the years my feeling seemed to be one-sided so I never revealed my feelings toward her. Since graduation, we'd talked a lot on the phone and Facebook, but tonight would be our first meeting since then and I'd be lying if I said I wasn't nervous. I shook the nervous feelings off though. Tonight was about fun and after the busy week I had I deserved some fun.

*****

It was nine 'o clock in the evening as Brian and I got ready to go out. After a hot shower, putting lotion on, and getting dressed: I found myself in front of the mirror in my room and liked what I saw. At twenty-three years old, I looked damn good. My black clean cut hair with waves in it was brushed. My smooth mocha skin was covered by blue jeans, a black t-shirt with an open tan button-up over it, and all topped off by a black leather jacket.

"Who are you trying to impress, D?" Brian asked, coming into my room.

"What?" I replied, looking myself over.

Brian laughed, "I'm just playing . . . you look nice, man."

"Thanks,"

"You ready to go?"

"Yeah, I'm not drinking though." I told him.

"Okay, just try not to nut in your pants when you see Sasha."

"Shut up,"

"You're going to talk to her right?"

I smirked, "Talking isn't a problem. Trying to fuck her might be,"

"Damn . . . and you're really not going to drink anything?"

"I might need a little liquid courage, but we'll see."

"Well, I hope you get that pussy tonight, D 'cause I know you're tired of fucking your hand."

"Yup," I admitted. "But I won't be able to just standing here, huh?"

Brian laughed and shook his head, "Nope, let's go."

A twenty minute drive later, we made it to Club Onyx. Getting out of Brian's car, our ears were filled with loud Hip-Hip and R&B. I rolled my eyes at this though. I loved the music, but I feared the party was going to be like this. Loud music, drinking, and when we entered the club, there would be a large mass of people on the dance floor. I was never really a party guy and began regretting coming out, but I wanted to see Sasha, so I decided to bear through it. Entering the club, I watched Brian immediately disappear into the crowd on the dance floor while I sat at the bar. Placing five dollars down, I ordered an orange juice. Sipping on my drink, I jammed out to the music.

Suddenly, I felt someone tap me on the shoulder and a familiar voice with a light Latin accent say, "Still drinking OJ when everybody else is drinking, I see."

Turning in my seat, I found Sasha standing before; my brown eyes liking what they were looking at. Sasha was a Dominican beauty with long, black, a buttermilk skin tone, and a curvaceous body. Sasha's beauty was only accompanied by her C cup breasts and round, bubble shaped booty. She was oh so sexy in the white blouse and short pink skirt she wore.

I guess I was staring too long because Sasha smiled and asked, "See something you like, Derrick?"

"Yeah," I told her instantly, giving her a hug. "You know you look good, girl."

Sasha smiled, "I'm kind of surprised to see you here. I know parties aren't you're thing, D."

"I actually just came out to see you," I told her. "Last time I checked parties weren't your thing either. Why are you here?"

"My girlfriends dragged me out here,"

"Hmm, why don't we go somewhere and hang out like we use to?" I suggested and to delight Sasha accepted.

"Let me go tell my friends."

I nodded, "Yeah, I've got to find Brian and tell him I'm out too."

"Meet me back here, okay?"

"Yeah,"

I found Brian dancing with some girls and told him, "Hey man, I'm headed out with Sasha."

"Cool, go do your thing bro," He said with a smile. "I'll see you later."

"Be safe Brian and don't get too crazy," I said giving him departing daps.

"Peace, D."

Sasha and I met back at the bar and set off to my apartment in her car.

*****

Back at my apartment, we sat on my living room couch and things were just like they were during our college days between Sasha and I. Our friends were partying and drinking while we were alone together making our own fun. We ordered some food, watched a few movies, and had ourselves a good old time. When the movies were done with we took the time to catch up.

"So how's school going?" Sasha asked, starting the conversation.

"Great," I answered. "Last time we talked you said you started a new job. How's it going?"

"It's okay. I work at Dave & Buster’s. The money's good, but if they like you, your reward is more hours on call."

I laughed, "At least you've got tonight off."

"Just be glad you're with a good friend, Sasha." I added, unconsciously placing my hand on her thigh.

Together we both realized what I'd done and Sasha simply smirked at me.

"Aww . . . don't tell me you still have a crush on me, Derrick."

In response, I gave her a look, "You knew?"

"Yeah, I was waiting for you to say something, but you never did."

I rolled my eyes, remembering my pining for her, "If I recall, I threw a millions hints at you, but you never took them. You kept me in the friend zone, Sasha. It was like all our friends knew . . . except you."

As I said these words I heard my tone rise in anger and took a few breaths to calm down.

"If you must know and I'm not going to lie . . . yes I still have a crush on you, Sasha." I said in a much softer tone.

Sasha sighed, "I'm sorry, D. I'm not trying to ruin the good vibe."

"I liked you back than too and what would say if I said I still liked you now?" She added quickly.

"I'd say this. . ." I trailed off with my words as I leaned in kissed Sasha's lips.

I knew my action was rash, but since being alone with Sasha again all my old feelings came rushing to the surface and they were guiding me at the moment. Our kiss intensified as Sasha wrapped her arms around me while I felt up her chest and caressed her soft legs. My hand trailed up her skirt towards her panties and found panties of soft cotton, but to my utter shock along with her panties I was touching her warm, throbbing . . . dick. The action came to a complete halt as I tore my lips from hers at this revelation. I backed away from her slowly and stood up off the couch.

"What was I just touching, Sasha?" I asked in a shocked tone, pointing at her skirt. "Since when do you have a dick?"

I didn't really know how to feel or what to do at the moment. I just needed Sasha to tell me something . . . anything, but she gave no reply.

"Tell me something, Sasha. I’m not going to tear your head off over it."

"I've had it since birth, Derrick," she admitted smartly, but weirdly I wasn't disgusted.

"So . . . you’re a shemale, Sasha?" I asked, being soft with her. "I understand why you didn't take to me in school now."

From then on we talked for fifteen minutes as Sasha told me all about her transsexual life. From coming out to her transition and after all of it I understood. There were no qualms between us about this. My old crush wasn’t what I expected, but I still liked Sasha regardless. On top of that (unbeknownst to Brian), I liked looking at shemale porn from time to time, getting off to it.

I sat back down on the couch and let out a sigh making Sasha quiz, "So . . . what’s up with us now, D?"

"Nothing . . . you’re still Sasha to me . . . and I've still got feelings for you." I said with pure honesty before kissing her again and yes I knew I was technically kissing a guy.

I was technically kissing a guy, but loving every single minute of it. Before my feelings just rushed to the surface, now they were spilling out of me in a blaze of overwhelming passion. Whether Sasha had a dick or not, it just didn't matter. All I knew was that after years of pining and yearning for Sasha . . . she was finally mine. What I didn't know though was that I'd do some things this night that a normally straight guy wouldn't and like it.

We began making out again and my hands went back to groping Sasha's breasts.

"Are you sure about this?" Sasha asked with a moan as I sucked on her.

"I'm sure Sasha . . . I’ve wanted this for so long."

"But. . ." She tried to say, but I silenced her with my index finger to her lips. "I want this . . . please don't make me wait another year."

Sasha smiled at my words, kissing me some more as I removed her blouse revealing her white bra. I removed her bra too and with her light brown nipples out in the open, I took them in my mouth I pushed her skirt away and after years of experience playing with myself, toyed with her cock. For my second surprise of the night, I found that Sasha was hung. Her dick was about nine inches and thick as hell.

"Mmm! Ahh shit," Sasha moaned as I stroked her dick slowly while licking and sucking on her nipples.

"Damn, you really want me, huh?"

"Mmhm," I mumbled with her left tit in my mouth.

Sasha removed her panties as I stroked her dick a bit faster, making it grow long and hard in my hand. I'd never touched another person's manhood except my own, but jerking off Sasha's was turning me on and my cock throbbed in my pants.

"Oooh! Mmm . . . keep going, D." Sasha groaned. "Keep stroking that dick, baby. I'm going to cum,"

I did as I was told, stroking her as fast as possible. I could feel pre-cum leaking in my boxers and planned to bust a good nut. Sasha's cock throbbed and thumped in my hand until her breathing quickened as she thrust her hips as she was about to orgasm.

"Fuck! I'm going to cum, I'm going to. . ." Sasha said though her words trailed off as her member erupted, spewing cum all over and it was a massive turn on.

Even though she'd just climaxed, Sasha wasted no time in pleasing me. She smirked at me, rubbing on my dick through my jeans.

"I see somebody likes playing with a dick, huh?"

I smiled, "Only 'cause it's yours babe."

My pants and boxers came away quickly as Sasha went to work, my hardness disappearing into her mouth.

"Um, yeah suck my dick, Sasha." I moaned, thrusting my hips as she was going to town on me.

My dick was close to nine inches long, five inches around, and curved to the left with a mushroom-shaped head and Sasha was taking the entire thing down her throat. Slurp, slurp, slurp, was the sound of her going down on my dick after she spit on it, making it easier to bob up and down on. She was slurping, sucking, and licking my chocolate stick while squeezing my balls at the same time. Once again, my mind not caring that a guy was swallowing my pipe.

"Damn, this shit feels good." I moaned, feeling myself about to bust though I didn't want to and told Sasha to stop before I could.

"Don't tell me we're done, Derrick." Sasha said with a frown.

"No, we're not done . . . I've got condoms."

"I don't have any lube though. Fuck," Sasha cursed herself.

I smirked, "We don't need any lube, baby. Turn around."

"Umm, umm yeah, right there, D!" Sasha moaned over and over as I was eating out her ass on my living room couch.

For all my life I was straight, but for this one night I was letting a bi or gay side (that I never knew I had) shine through.

"Oh shit!" she yelled as I stuck my tongue in her already dripping-wet ass.

I rimmed Sasha's ass in circles, in and out like it was a woman's throbbing pussy. I was eating her out so good that she started grinding against my tongue as I entered her ass at rapid speeds. I loved every moment of this encounter while my conscience was screaming, "You're straight," but every other part of me screamed louder to finish making love to Sasha. I was licking her ass crack up and down while playing with my dick, taking me to ecstasy.

"Oh shit, goddamn!' she howled as I dove into her with two fingers, preparing her for my dick.

Sasha went back to servicing my dick. She was so good at giving a blowjob. Sasha continued to bob up and down my dick only stopping momentarily to take both my balls in her mouth.

"Yeah baby, take my dick!" I shouted as I shoved my dick down her throat and didn't gag once.

Sasha stroked my cock making it as hard as ever, "Mmm . . . are ready, Derrick?"

"Yeah," I replied as she handed me a Magnum condom.

This was my first time fucking a guy or shemale (whatever), but I was like, what the fuck. I put the condom on getting ready to punish Sasha's ass. I bent her ass on the dining room table then took two fingers and eased them into her ass like earlier. She started squirming, gyrating, and pushing her ass toward my fingers like he couldn't wait for me to put my meat in her ass. After a couple of minutes of stretching her ass muscles I took my fingers out and slowly pushed my dick in her warm ass.

"Damn!" I groaned as my dick seemed like it was getting sucked in her ass.

The feeling was blowing my mind. I began pumping her ass slowly, holding onto his waist. I took my cock out and with one quick motion I rammed myself back inside.

"Ahhhh," Sasha yelped as I was pummeling her ass with all nine inches of my dick and she was taking it well.

I pumped and pumped until I was drenched in sweat. I flipped Sasha over on her back, putting her legs on my shoulders. I pushed my dick back in her hot, waiting ass and began plowing her again. I was pounding her ass so much that the table started to squeak and rock as I felt myself about to cum.

"Oh shit! I'm going to cum, Sasha," I warned, groaning and moaning as I came close to orgasm.

I pumped into her as much as I could, feeling my legs getting weak. Next thing I knew I felt my leg cramp up as I filled the condom I wore with my man milk.

"Fuck!" I screamed, falling forward onto Sasha completely drained of energy and bodily fluids just as Sasha's dick shot out her second nut of the night.

Sasha wrapped her arms around my neck as we were suck there, neither of us having the power to move. After years of wanting Sasha and finding out that she was a shemale was quite a shock, but shemale or not this sexual conquest was definitely going down in my book as one of the best I ever had.

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than Lushstories.com with this note attached, it has been posted without my permission.

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Comments(8)

naughtykellypreston
Posted 19 Mar 2014 17:33
Amazing story, very well thought out, and very well told.
christyt
Posted 10 Jun 2013 12:49
Loved it, made me so wet reading it. Well done!!

Buz
Posted 04 May 2013 07:08
Great story dude!
Vic
Posted 29 Apr 2013 20:38
great well told story
Shaven
Posted 29 Apr 2013 14:27
Very hot
oklahomaguy
Posted 29 Apr 2013 10:53
Great read

stockingluvr
Posted 29 Apr 2013 10:39
Loved the story!!! Tell us more.

Green_Man
Posted 29 Apr 2013 10:22
Nice work. Love a good tranny story well told.
 

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