How I Met My Shemale Pt. 02

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Shy man dates shemale.
1.5k words
4.44
75.3k
71

Part 2 of the 4 part series

Updated 06/07/2023
Created 04/02/2014
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I sat motionless and stared at her as she swirled her thumb around the end of her glistening member. It was very well lubricated with her sex fluid. "Hey you! Don't you know it's rude to stare?" she shouted, breaking the trance I'd been lost in.

"Oh, sorry," I said as I glanced up at her furtively. She was murmuring something to herself while drawing her slick, black panties up her stocking clad legs. She seemed to now be guarded of her surprisingly large male appendage, now hidden under a layer of tight latex.

"There, happy now? I'm all woman again, just for you." Her voice had a slight tremor to it. I looked up at her again with growing confidence. Our met eyes briefly. Hers were searching mine, mine were questioning and wide. She looked like she was about to say something, but her expression changed to one of anger and in a flash she lunged towards me. I had forgotten my wrists were still tied to the bed post. I twisted at the waist and closed my thighs tightly together, in an effort to protect myself.

"Oh fuck! Give me that mess of yours!" she said as she tried to force my legs apart. I resisted, thinking briefly of crying out for help. She persisted in trying to grab at my come filled condom and penis and drove her foot with its high heeled shoe into my groin, for leverage. I groaned in pain and humiliation as she pulled the sheath from my exhausted manhood, far more roughly than necessary.

The sex toy egg it had contained bounced off my knee and fell to the floor with a thud. She held the used condom directly in front of my face as she wrung it between her fingers. I watched as my semen squished out across the top of her hand. She glared maniacally into my face, nodding while shaking her fist, expelling the sperm within messily.

"Enough! Untie me already!" I demanded. We were both taken by surprise by my new found assertive voice.

She grabbed me roughly by the shoulders and slammed her knee, her sexy, stockinged knee I had admired so much, right into my testicles! I tipped over while bringing my knees up to my chest in agony.

She asked with true contempt, "Why should I? You want to run away now?"

I still lay on my side with eyes shut tight, my wrists twisting in vain against my restraints when I felt her pulling my hair. She said, "Here, look at this. It's showtime." I opened my eyes reluctantly.

"Oh no," I said in disbelief. What I was seeing was video on her iPhone, a video of me blowing her, making a complete slut of myself in the process.

She added, "And don't you look handsome, swallowing hard cock like a horny bitch! I just might be emailing this to... Oh well, I'll think of someone..."

I closed my eyes again and said firmly, "You don't have to do this. I have no plans to leave you. I lo..." My words were cut short by hers.

She growled, "You what? You're going to tell me you love me now? I'm a freak. You don't love freaks, you use them and discard them."

I searched myself for what to say. I responded honestly when I said, "You're no freak. I want you, all of you. Nothing's changed. Please untie me."

An eternity passed. She untied me, as I had asked of her. We kissed and held each other silently. I was in ecstasy loving her like a man loves a woman, an exotic and rare woman.

Naturally I had some questions. She answered them all. Yes, she was born that way. No, she had never been found out, not since many years ago anyway. Best of all, I was the first she had ever gone so far with. After considering all she had confessed, I could only say, "Must have been hell, growing up with a secret like that."

She laughed, "Well it's not like I went waving it around for the world to see..."

God it was good to have her laugh, but wait, would this change her attitude in bed? I had to admit to enjoying being controlled by my forceful shemale. I was about to broach the subject when she removed all doubt.

"Okay, a promise is a promise," she said, as she slid out of her panties. My mouth watered as I gazed at her now. Her hard inches throbbed with a new life of its own, bobbing around like a club beneath the frilly hem of her corset. There wasn't a trace of shame between us. All I wanted now was to have sex with her.

"First let's pretty you up a little," she chortled, gathering some lingerie items together seductively. Soon, I was decked out in a pair of her stay up ladies stockings and a pair of crotchless panties. I was a bit shaken by this as it had been a while since I'd experimented with cross dressing. "Mmmm, don't you look sexy now?" she purred as she adjusted my stocking seams and admired my willing body.

I slid my hand instinctively down to my own erection. I was harder now than I'd ever been. She slapped my hand away and said, "No, bad girl! No touching! It's all mine."

Instead of administering another cock sucking, that I so wanted, she spun me around and tied my hands together behind my back. I trembled before her. I knew she was going to take my ass virginity and there was no stopping her!

I climbed awkwardly onto the bed and assumed the position. My quivering buttocks were hers to use and abuse now. My face was pressed into the pillows. I sighed and prepared to be taken. She wasted no time. I felt the bed shift as she got behind me and tied a black stocking around the base of my cock and balls. She gave the tether around my engorged sex organs a hard tug. She laughed "There, now you're ready for a thorough fucking."

She ran her sharp fingernails up and down my back with one hand while she gripped her throbbing hard on and slid it roughly between my ass cheeks. She started at the top, missed my anus, continuing down to base of my hard cock, giving the area a good nudge for good measure. This was driving me crazy, I now wanted her inside me. "Beg for it. Beg to be fucked you hussy!" she said playfully.

"Oh, give it to me. Give me your beautiful hard rod!" I said, hardly believing what I was requesting.

She responded, "Louder! Louder, I don't believe you!" she responded while pulling my cock leash hard.

"I want it! Shove it in me! Mount me!" I shouted. There was a loud banging on the wall. The people next door were not happy with us. This amused her and she slapped me across the ass, giving my cock leash another satisfying yank.

She giggled, "Bad girl! You've forgotten who gives the orders!" She rolled me over onto my back and got on top of me. Her bottom was hovering over my erect, shiny tipped member. She grasped my rod and pressed it against her tight asshole. She was pumping at her own cock, causing it to spill precome on my panties. I thrust up at her, bumping her sensitive opening rudely.

She lifted her hips just out of range of my solid manhood and seethed, "Oh, now you've done it. I was going to let you come into my greedy little hole but now I won't let you." With that said, we were back in position, with her teasing my now slick and wanting man pussy with her bulbous glans. She worked her cock head into me, just entering me an inch, then withdrawing. I felt a sprained sensation as my hole was being opened and readied by her. She kept on, in-out, in-out.

Just as I was about to thrust back at her, she took full control. She grabbed my hips an impaled me! I was shocked at my feelings of sudden fullness and gasped.

She sent the whole of her savage erection all the way in. We stayed locked together that way for a moment. I rotated my buttocks against her thighs, rough stocking tops and her heaving belly.

She exclaimed, "Ah! There! Oh fuck this feels good! You're all mine now. Do you think you're worthy of my fucking cream?"

Before I could answer, she slid fully out of me, then back in, ferociously! She started pounding me hard and fast. My scrotum pulled up tight and I felt a new and urgent warmth spreading and building within me. I was going to come soon. Unaware, she kept her pace, fucking me forcefully, concentrating only on her intense pleasure. One more pull at my cock leash did it. She had angled her erection down atop my male G spot, causing me to come hard, all over the bed spread.

My rectum and anus spasmed around her shuttling shaft and sent into an ecstatic orgasm of all her own. She cried out, "Oh you little bitch! I'm coming...Ooohgod...Fuck! fuck!" She tried to pull out but I clenched around her erupting member and enjoyed jets of hot semen squirting into my depths, satisfying me beyond what I would have ever imagined.

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5 Comments
AnonymousAnonymousalmost 9 years ago
Tied and teased

Oh what a tease she is

hardatwork1981hardatwork1981about 10 years ago
Yummy

Damn I would love to have a sexy shemale take my ass virginity this way!

AnonymousAnonymousabout 10 years ago
Nice read

They could subtitle this "The Great Cornholio"

AnonymousAnonymousabout 10 years ago

he got her now she is his to command more chapters

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