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First Date with A T-Girl (Part 2)

"It was their first date, a few laughs and a quiet drink."

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Author's Notes

"I hope I’ve done this second part justice and I hope people connect with Kay’s character or maybe even Daniel’s attempt at being slightly different."

It was awkward trying to walk and jiggle her knickers down her legs so that they fell to the floor as Kay walked back to the bedroom with a gin and tonic in each hand, but she managed it. She rounded the bedroom door stark naked to see Daniel flat out on his back, hands spread to the side, eyes closed and legs open. At least, he had removed his gurly panties.

Kay leaned against the doorframe and watched him; drinking in the sight of him on her bed. Every detail of his body made a bee-line for her eyes, filled her senses, corroborated and conflicted with what she found sexy in a person and she slowly came to the conclusion that Daniel only fulfilled fifty percent of that. She felt a knot form in her throat. A sense of disappointment, not a real one, rose within her.

It was true, Kay was attracted to the more feminine looking of the species, even women attracted her attention these days, but in reality a lovely feminine T-girl like herself, maybe with bigger breasts so that she could suck on them would have been her ideal partner and lover. Not that this first date had transpired into anything like that, far from it. From the waist down, Daniel could easily fit the bill. It was the chest hairs and stubble on his face that perhaps let him down the most. Lots of things didn’t ignite that fire inside her, and yet –

She had started down her road of discovery in the same way, cross-dressing. Yet, Kay felt a much stronger pull towards the feminine side of her persona, much more than the male side, and while cross-dressing could be hidden behind closed doors, true femininity came with a price tag and she wasn’t thinking about the clothes and shoes that would need to be purchased. It was a struggle at first, and then came the embarrassment when all the family members realised her intentions. She knew she wanted her outward appearance to be feminine but was unsure about all those drugs and ongoing operations; turning things inside out didn’t appeal to her.

She was lucky in some respect that her body shape afforded her the luxury of being able to choose all the right clothes and when she did make that change to female it would always be after work.

As time went by, coming home from work was a relief in more ways than one. At least, her job was over for the day and her man clothes were thrown to one side and a new set carefully chosen from the wardrobe. Yes, it was a double life and she felt far more comfortable in one than the other, which was why she related more to feminine-looking T-girls than anyone else. Not that there were that many around where she lived.

Daniel, on the other hand, looked like a man in every respect. Yes, he had made the effort and that in itself was why he was there, in her bed, naked. She was intrigued by the images he sent her in the emails they exchanged, intrigued by the artistry of them more than anything, he was certainly talented in that respect. She felt comfortable talking to him and when he suggested what he’d wear on a date – well, that’s when she found out that she couldn’t refuse.

Her mind, the one in her cock, took control and she couldn’t think of anything sexier than a date with a closet crossdresser that hid the sexy underwear under their normal clothes. It had to be done.

Looking at Daniel from the waist down made her feel rather horny. She took a quick intake of air into her lungs and breathed out slowly as she traced the black lingerie from the suspender belt down the sides of his legs. The sheer black stockings with their lacy tops were rather fetching. She could certainly fuck him, she thought.

Her cock twitched, not once but twice. She would have grasped it and tugged at it if her hands were free; she’d have even pinched her nipple.

In all the while she watched him, he never stirred; he was happy to just be splayed out on the bed, relaxing.

“I know you’re there,” he said, he must have heard the cogs turn in her head or her penis rise from its previous ashes, or more likely the intake of air as she breathed.

His words came as a bit of a shock to Kay, she pushed herself off the doorframe and walked towards the bed, her cock growing with every step and her grin becoming wider. She took a large sip from one glass before placing both of them on the bedside cabinet. Her cock swung as she swayed to position herself over Daniel’s body.

His hands came upon her waist, “Is this lovely gurl going to fuck me?” His lascivious smile hinted at a secret desire.

Kay shook her head. “Nipples first,” she replied.

Kay shimmied down the bed until her head was above Daniel’s nipples. Her fingers came in from the sides of his body and she started to circle them around both nipples at the same time. She was impressed with the response, especially from a man’s nipples. They just seemed to grow and stiffen, the areola crinkling under her spell. She could feel his cock slither and slide under her stomach as it too, responded.

With both fingers outstretched, Kay started to flick rapidly against Daniel’s stiffened nipples. The rapid twitching caused him to moan. He lifted his head from the pillow to look at how she handled them.

“That’s fucking lovely,” he said. His cock twitched against her tummy. “Flick them hard,” he continued to instruct.

Kay did the opposite she flicked one and clamped her mouth down on the other and sucked hard on it.

“Oh, fuck! Bite it,” Daniel’s response was immediate.

When her teeth clamped down on his protruding nipple, Daniel let out a loud gasp. Her mouth had immediately transposed to the other nipple and she sucked and bit a second time. Alternating between the two, Kay could feel Daniel’s cock stiffen beneath her and her cock become engorged.

She immediately pulled herself upright and sprang from the bed, she opened her bedside cabinet to retrieve the KY jelly before getting back on the bed and positioning herself so that their cocks were together and Daniel’s leg in the air, nestling between her tiny tits. She squirted some lubrication onto their cocks and balls and started sliding her bottom over his leg; squashing their shaved and silky smooth balls together as she approached his outstretched leg.

Daniel had seen this done between two women many times while watching porn, but never with a couple that sported cocks. He made a mental note to look it up on his favourite porn channel when he got home, but right at that moment, he pushed back in the direction of Kay’s energetic fucking. To Daniel, it felt sexy and the motion of their bits squashing together was rather pleasant.

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Kay eventually let go of Daniel’s leg and ended up on top of him, thrusting her cock alongside his and humping his groin like a dog on heat. She could feel the hotness of his dick against hers and the pent-up desire for her to cum was instrumental.

“I wanna cum,” Kay muttered as she humped Daniel’s groin. Her eyes closed in concentration.

“I wanna cum. I wanna cum. I wanna cum,” her words reinforcing her need on every thrust.

“Oh, yes, that’s it, that’s it.”

Daniel was feeling her pleasure, though not as much as Kay was living it. Her thrusts became slower as her orgasm took its toll.

“Come in my mouth,” instructed Daniel.

Kay scrambled up the bed and presented her cock to Daniel’s mouth, she let her body pulse twice before she squirted cum to the back of Daniel’s throat, her stomach clenched and unclenched every time she ejaculated, her hands came upon the headboard to steady herself as Daniel sucked gently on the end of her pulsating dick and cupped her smooth balls in his hand; encouraging them to release all that wonderful juice. His other hand stroked the side of her thigh and he wondered whether a finger in her ass would be too much for her to take right at that moment.

When the volume of fluid subsided, Daniel began to remove himself from under Kay, she slipped to one side and before she knew it she had been pulled down the bed. Daniel was swiftly upon her, his cock straining and seeking the entrance protected by her dark star. His cock was already coated in the remnants of the KY jelly they had used earlier. He pushed into her, slowly at first and then when her star started to open he let it slip in.

Kay sighed, he felt big inside her tight ass.

“I hope you’re ready,” he growled, “because you’re about to get fucked like a gurl.”

Kay’s eyes widened. She was impressed with his demands and secretly couldn’t wait for him to carry them out. Her smile belied her need to feel him take her.

“Yes, fuck me. Do it,” she growled into the pillow. Her hands clenched the sheets on either side of her as she waited for the onslaught.

Daniel started to thrust, taking his time and slowly removing his cock so that the tip was just inside before pushing rapidly back into her bottom. The lubrication helped a lot and it wasn’t long before his thrusts and use of language excited both of them. He knew, deep down, he wasn’t going to last long in her tight ass.

“You like being fucked like this,” Daniel started the conversation while his cock began its rapid decline to climax. His pounding became more and more rapid, urgent, demanding and uncontrollable.

“Yes, yes,” Kay replied.

“You want my spunk up your ass, don’t you? Tell me you want it.”

“I want your spunk up my ass. Fill me with it,” she clung to the sheets wanting him to pound her senseless.

“Fuck it’s tight, are you squeezing it out of me.”

She had indeed started to clench her buttocks on his rigid cock; a technique she knew would bring him closer much quicker.

“I’m cumming too. Don’t stop, I’m going to cum. Fuck me ‘til I cum.”

She could feel his cock constantly brush against her prostate which only served to pleasure her more than the act itself.

“Yes, cum on the sheets, Kay. Let it all out.”

“Oh, fuck, yes. That’s it, Daniel.”

“You dirty little fucker for cumming again,” Daniel scolded her and pushed his cock into Kay’s bottom for the last time. He held it inside her and let his spunk flow into her deepest channel. Her juices shot from the end of her cock and pooled on the sheets below her.

Daniel remained deep in Kay’s ass until he was fully spent. When he pulled out, he rolled her body to one side to reveal the mess she had made. He quickly sucked it all into his mouth.

“Warna share,” he gargled, making his way up the bed. Kay pulled him down for the kiss and tasted her wonderful spunk as it swirled and smeared their lips; spunk she had tasted many times on those lonely nights.

They rested for a while, spent and sated for a third time that evening. It was an evening that was rapidly coming to an end. It was Daniel that made the first move to leave. His work demanded that he make an early start, it was unavoidable, and so, and with much regret, he slowly got dressed to make his way home. It was a torturous attempt at leaving but he needed to.

Finally, he removed his stockings and suspender belt and bundled them up along with his gurly panties into a supermarket plastic bag that was so kindly donated by Kay and he wondered whether he would need to return them at some point soon. He dressed before sharing the final kiss on the doorstep.

The door swung closed and while leaning with her back against it, Kay was left with her thoughts and feelings. How many times had they cum? God, he loved spunk, didn’t he?

In the bedroom, she spied both drinks on the bedside cabinet. The ice had melted but she downed one and kept the other for later. She headed for the shower. Feelings poured from every orifice as she washed the sins of the day down the drain. It was certainly an eventful evening, she thought.

ooOoo

After that first date, Kay decided to not proceed with a second date. She let Daniel down slowly and carefully. It was the right thing to do and he seemed to take it well. They chatted for a while via messenger and during one of their more flirty sessions, she sensed that towards the end, his responses had become a little guarded.

Is anything up? Kay asked.

His response was immediate. Naughty you, of course, something’s up!

That’s not what I meant and you know it? she messaged with a smirk on her face.

Nothing’s up. It was just that I had hoped you’d have fucked my virgin ass on that first date, that’s all. Daniel replied.

Kay stared at the message for ages. She felt her nipples harden, she felt her cock twitch in her panties and she felt that urge rise through her chest. Her head and eyes lifted towards the ceiling and she sighed heavily.

Fuck! she thought, biting her lower lip in anticipation.

Is anything up? Daniel asked.

Published 
Written by DarkSide
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