Hey, Lemme See That

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Crossdressing

I hung out with Kimberly all the time back then. She was a cute girl, but she hung out with the boys, like a boy. That being the case, she wasn’t a girl we chased. None of us did. I can’t speak for the rest of the guys in the crew, but acting like she was just one of the guys was a bit of an act for me. There’d been a hint of flirtiness between her and me in the past, but it was pretty much just a footnote to a storyline that was pure friendship.

One morning she came by my apartment to get me out to do stuff. I was still in bed, and she was putzing around the room just talking about whatever, stuff to do mainly. She got tired of waiting and told me to get out of bed. She was sitting on the right corner of the bottom of my bed, and my closet full of clean but unfolded laundry was on the other side, near the head of the bed. Not feeling like I was pushing the boundaries of our casual relationship too much, I slipped out from under the covers and turned to the closet. I was naked and more than half hard as mornings would have it. I knelt just inside the closet door to grab the first pair of underwear and jeans I could find. Looking back and being honest, a deep seed of that part of me that definitely saw her as a woman prompted my decision, because it got off on the idea.

As I stood up, back still to her, she said, “Hey, lemme see that.” She was pointedly nonchalant in her tone.

I just stopped moving for a second and she followed up with, “Your dick. It’s hard. I wanna see it.”

I dropped what I’d picked up and turned around to face her. She watched me go through a five second transition from a little more than half hard to impressively swollen and pointing at the ceiling. Voluptuous with black curls wasn’t my usual modus operandi, but with Kimberly in particular, I was certainly enjoying this new freedom of taking in her beauty in such a blatant and open way. She was neither shy nor brief with her gaze, and I struggled to fight off any demons of self-consciousness. To lock in the casual spirit of what was happening, and to keep from fidgeting, I turned to walk over to the CD player on the shelf across the room. I had to pass right in front of her, prick bobbing with each step. I milled through the CDs, not really registering what I was looking at.

“Would you have had a hard on if I hadn’t been in your room with you naked like that?”

“Most mornings, yeah.”

“And you’d jerk off, wouldn’t you?”

“Yeah…I suppose I would.” I settled on a Ween CD. Pure Guava. I slipped it into the player and hit play.

“So my being here… umm, it’s kind of interrupted your- routine I’m guessing.”

I just took a deep breath. It certainly wasn’t the first time she’d interrupted my “routine”. Her gaze returned to my situation for emphasis as she said that word.

“I want to see you do it,” she added, more coyly than casually now.

“Seriously? You mean you want to watch me, like, get myself off?”

“Oh come on. You’re practically dripping. I’m pretty sure you need to do it as badly as I want to see it.”

I took the liberty of touching myself, not with purpose; just the way one does in an environment of privacy.

“I’m excited by the idea. I’m not gonna lie. I’m just a little worried I’ll be violating something or breaking something. It’s hard for me to articulate I guess.”

“Seriously, the only thing you’ll be violating or breaking is the shroud of bullshit that keeps us from ever even discussing this sort of thing in the most abstract terms. I’m telling you to fucking jack off for me. I think that means I’ve already broken whatever goddam thing that could possibly escort ataşehir break.”

“OK then, I want to see your tits.”

I was testing the water, and the mood seemed to call for that vulgarity. I wasn’t sure she’d allow me that much control of the script, but she immediately pulled her red v-neck sweater off over her head and reached back to unclasp her bra. Her breasts fell free, and my urge reached the point of fever. I’m not even really a breast man, and bigger tits never did all that much for me. This was incredibly hot though. They challenged my prejudices with their youth. Their- how to say it without being trite of puerile- their levity.

“You want me to just stand here and do it? You want me to lie down in bed like I’d usually do it. Shit, I don’t even know where I should cum.”

She laughed, “Where would you usually cum?”

It was a little embarrassing to divulge what was almost always a private event but, “In a washcloth, I suppose.”

“Come stand in front of me where I can see it up close. Don’t even worry about where you’re going to cum. Just let me see.”

So, I walked around the bed and stood right in front of her. I started to manipulate my balls a bit with my hand and pulled them back so the skin on my cock stretched tight. I was about to move my hand to my cock when she stopped me.

“Wait a sec,” she hesitated. “Can I slap it?”

“You want to slap my fucking dick?” Almost a laugh.

“Yeah. Not really hard, but it’s so… fucking stiff. I just want to fucking slap it and watch it… you know, bounce back in place. Please?”

I sighed and, somewhat to my own surprise, agreed. She took my dick between the tips of the middle finger and thumb of her left hand at about mid-shaft and gave a couple little squeezes. That pressure alone was almost completely overwhelming.

“OK. I’m going to slap it three times, but first I want to clean some of this stuff off,” she said, wrinkling up her nose but still with a playful eye. “Otherwise, it’s going to go flying everywhere when I smack you.”

She moved it back and forth, tilting her head with each motion to suggest an official assessment of what needed to be done. She leaned in and positioned my penis with her finger hold so it would meet her lips. She pushed her bottom lip to the underside of the head, and using her fingers to pull the skin taut she pulled her lip back to the tip, gathering the pre-cum that I was producing at an almost startling rate. Locking her eyes onto mine, she used her top teeth to draw the wetness off her lip and into her mouth. Her lips came together as she swallowed just that little bit, and she repeated the action with her top lip and bottom again, several times over, until she’d pretty much dried it completely. She brought her left hand up and gently took my balls in her fingertips, caressing the underside of them with her fingers. It was such a tender series of motions that the shock of her slapping my cock was like falling into an unseen pool of water. It really wasn’t unpleasant at all. In fact, I was excited by my awareness that she was about to do it again.

Her gentle attention to my balls seemed to take on the purpose of making up for an injustice, like a tender, tactile apology. Her eyes though, they were searching mine for the reflection of the sting of the slap. And again, she struck it from the other side with the back of the same hand. It bounced back and forth several times, and it felt like the drawing of the my very skin under that motion was stroking tension underneath it.

“Oh nooo, you made more wet stuff. I guess I’ll just test kadıköy escort my theory about it flying everywhere with my next slap. You know, when that moment comes.”

She moved in close like when she’d put her lips on me before, but this time she brought her eye level to my balls and stared at my dick like a child looking at a bug in a jar. She’d tapped right into my exhibitionism, and her stare was almost as intense as the feeling of her mouth had been on it.

“Your balls have tightened up a lot. You must be about to spray everywhere.” She paused. “You know… looking up at the underside of your shaft somehow seems more obscene. It makes me feel particularly dirty, especially up close like this. It’s like staring at the belly of the beast. I can even see your pulse in it.”

Curling her middle finger up under my balls she traced a line with her fingernail from behind them, right around the seam to the front, then up the middle and slowly along the underside of my dick upon which she’d so graphically reflected just a moment ago. She slapped my dick again, so hard this time that it slapped my body four times as it swung back and forth. I felt like I almost came, and the tremor in my gasp gave it away. She cut her eyes up at me and smiled slyly.

“I think it’s time for you to stroke it now. Now, would you like me lying back so you can stare at my tits, or would you rather I keep my face close?”

“Lie back for now. I fucking love the sight of you topless over those snug, faded Levis.”

She did as I said, and she shifted her torso downward and her hips up a little. Her eyes went to almost closed as she caught a small gasp of a breath, and I could tell she was taking advantage of the seam of the jeans between her legs. I moved up onto the bed, upright over her, on my knees. I positioned one knee between her legs so that she’d know she had the option of sliding down just a wee bit more and finding whatever pressure she might want at any moment. I gripped myself and began slowly stroking. I paused after a few strokes to caress and knead my balls, then give my shaft a rather hard squeeze. I began stroking again, picking up the pace a bit. Her eyes shifted back and forth between my eyes and my cock, and her breathing picked up pace as I did. She shifted down again, against my leg just as I’d hoped, and I could feel the fleshiness of her labia through her jeans as she pressed against my leg. Now she was rubbing it up and down on my leg, bringing herself into synchronicity with the rest of our motions.

“So, you given any more thought to where you want to cum?” She just barely managed to get that out through her heavy breaths.

I moved my hand a little more slowly and with a tighter grip, forcing more pre-cum into the world.

“I have a few ideas” I said, pressing my dick downward with my thumb, then letting it pop back up.

“Tell me three.” She had one arm back, hand behind her head, and she grabbed the top of her jeans to pull them up tight against her. “Mmm…That feels so good pressing into my cunt. You see?” She slid herself up my thigh to angle her womanhood toward me, as if for inspection. “Now tell me about your ideas.”

“Well, if I just keep going like this, I’ll cum all over your tummy and tits. Some might hit you in the face too. That’s all kind of a turn on.”

“Yeah?” she whimpered, “I’d wipe it up off my tummy with my fingers and eat it.”

My eyes widened at her words. She knew exactly what to say to bring me closer.

“What are your other ideas, sweetie?”

I was just squeezing the sides of my shaft at this point, enjoying the pressure maltepe escort bayan but trying to hold off what was coming. Kimberly, had found her rhythm against my thigh, and she was picking up her speed and intensity.

“The way you had your bottom lip under the head of my dick a few minutes ago. I was thinking we could do like that again and I could kind of cum in your mouth.”

“That’s definitely hotter. It would also save me some effort in swallowing it. You do want me to swallow it, right?”

I started stroking again, harder and a little faster. My breathing was getting faster and harder as well.

“You’d better hurry up and tell me your last idea” she said. She brought her right hand up to her right tit and was playing with her nipple, forcing it over with her fingertip, pinching, and tugging it.

I sighed deeply, as the next thought might be a little too much. “I’d like to rip those jeans off you, push your knees up by your ears, and cum inside your pretty ass.”

She stared up at me for a few moments, letting me stew in my anticipation of her response.

“You want to fuck my ass, baby? Yeah? Hmm. Why not this?” She traced the seam of her jeans where it was stretched over her pussy.

“I want to eat that after.”

“Hmm… fuck my ass and lick my cunt. Stroke faster- I need to think.” Her thinking seemed to be speeding down a path toward both of us cumming before she made a decision.

She was pulling harder on her nipple, stretching it and the skin around it farther than I thought it could stretch. I began jerking myself like I was getting ready to blow, and I could feel the buzz of approaching orgasm.

“I definitely want to feel you push your dick in my ass, and I’m most definitely in the mood to fuck YOUR face now. *sighs* But…”

She sat up and leaned in toward my dick again. I was fighting for control.

“For now, this is all about your morning jerk off session I so inconsiderately interrupted, so I think we’ll go with that in-my-mouth idea. You think you’re almost ready?

I nodded, as I couldn’t even answer. She positioned herself with her hands down on the mattress, making minor adjustments as her weight steadied between her sexy shoulders. She pulled her black curls back over her shoulders and out of the way and leaned forward. She pressed both of her lips against my balls and kissed them. Then she moved up to my cock and opened her mouth wide. I pressed the head down on her bottom lip firmly and began stroking a little more slowly again. As I stroked, I also, almost imperceptibly moved my cock back and forth, letting her lip stroke under my dick, just behind the head. I could feel her teeth pressing up through her lip. Her eyes locked on mine as my moment approached. I said Oh God. I turned my pace up to a frenzy and looked down at that pretty face. I looked into her mouth just as her tongue flicked to add to my stimulation, and my semen exploded onto her tongue. The pressure was still building though, and a second shot erupted as she closed her lips around me. I was now fucking her mouth in small strokes, working the last of it out.

She reached up and massaged my balls, helping to knead them out of their contracted state. She continued to suck on me, and I started to buck. I was too sensitive to take anymore. I fell backwards onto the bed, and she sat up, still rubbing my balls. I was so spent that spasms kept running through me. She grinned as she looked down at me, obviously pleased with herself.

She leaned in close to my ear and whispered, “Rest up. This day is just beginning.”

She slid off the bed and stood up. She unzipped her visibly dampened jeans and slid them down her thighs along with her a pair of satiny, bright blue panties. She was mostly shaved, more than a bit puffy, and clearly, clearly ready for some attention in return. I could already feel myself stirring again.

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