All the Feelings by Amy Brett
I met him at the partially opened door in the way he had told me he wouldn't mind. His only real requirement was that the first time we met in person, I had to be fully dressed in nice female clothing and with as much of an attempt at makeup as I could achieve. Other than that, he would accommodate most anything.
"Hi," I said as he came fully into the living room and allowed me the space to close and re-lock the door.
"You're right," he said enigmatically. "Your face probably wouldn't pass but your body is magnificent." At 5-7 and 130 pounds, my shape was reasonably good except my waistline that was probably a little thicker than most women's. Only the breast forms nestled in the bra made my chest look feminine but simply shaving had made my legs look as good as any woman I'd seen. With the thigh high stockings holding them, they looked spectacular.
My long brunette wig took care of that detail and the soft peasant blouse and short skirt rounded out the illusion that all women used. White strapped city pumps changed the shape of my calves and made me 3 inches taller than normal. A high cut but soft sport panty effectively held my softened secret back between my legs.
My attempt at taking care of my face only included a thorough shave, eyebrow pencil, a little mascara, and dark lipstick.
I'd seen Bill's picture when we talked in the chats but his presence was different. At about 6-2 and probably 200 pounds, he was much larger than me. Generally, he was just a great deal more masculine.
Muscular biceps and forearms, covered with dark hair, extended beyond a short sleeved designer teeshirt with a collar and pocket. Tight, the shirt showed off a muscular chest and just a moderate middle aged spread at the waistline. Tan slacks with a solid crease covered larger hips and what I was sure were equally muscular legs. Mocassin-like slip on shoes and white socks finished out what I could see of his clothing.
His face wasn't particularly good looking or even very noteworthy but, smiling, he looked pleasant enough. His receding hair was black and thick. His twinkling eyes were almost as dark as his hair and his mouth was filled with sparkling white teeth. Though it was before noon, he already had a slight 5 o'clock shadow.
I'd stopped there at the door, trying desperately to figure out what came next.
"Would you like something ..." I began but, luckily, he took the matter out of my hands. Totally self-confident, he took a step toward me and, foremost, I felt my personal space violated. In a kind of defensive way, I put my hands against his chest as I felt his close around the sides of my waist. He wasn't in danger of being able to reach around me but I felt how close his big hands got, his fingers almost to my spine and thumbs squeezing softly into my stomach.
This close, I could smell a little accumulated perspiration from the drive, feel the hardness and mass of his chest, and really know how much bigger he was than me as I looked up nervously into his eyes. He smiled as he pulled my waist tight against him, turned his head slightly, and moved his head close enough to kiss me.
I felt the brush of his stubbly skin against mine as his lips touched mine. Strange that my reaction should be a gasp but that's what it was. It couldn't have been surprise but, in a few heartbeats, I realized that it was and the cause of the surprise was how much I liked it. Shakily, I lifted my hands to his shoulders removing the impediment to his being solidly against me.
His tongue probed gently at my already partially opened mouth, his breath and mouth both reflecting either a breath mint or piece of candy. I opened mine more and felt it move in much further as I turned my head and shut my eyes. His hands left my waist, one moving to the base of my spine and the other just below my neck. He moaned as my hand found the back of his neck and held the kiss even more tightly. My mouth watered.
My tongue explored his in my mouth and followed it back into his where he sucked it with increasing fervor.
I have no idea how long the kiss lasted. I do know that it was time enough for him to explore my head and neck with one hand, stroke my back, and finally explore the back of the skirt thoroughly. All I could do was hold on to him, explore his neck and the back of his head, and gasp with the pleasurable feelings his hands and mouth on me imparted.
I also noticed his hardness pressing against my stomach and the pain of my tucked maleness.
Finally, he loosened his hold on me, wrapped his big hands around my upper arms, pushed me away a little, and smiled.
"I'm going to take my clothes off now," he said with a smile. "But all I want you to do is refresh that makeup a little. Okay?" I nodded and watched him lift his shirt over his head in a motion. He stopped, looking at me from a few feet away, as I saw that his chest was every bit as muscular and hairy as I'd expected. "Lipstick, sweetheart," he said as he kicked off his shoes and started undoing his pants.
Staring as I moved in the general direction of the bathroom, I saw him uncover powerful, hairy legs and red underpants. Quickly, I slipped back into the bathroom, adjusted the wig that had slipped back a little, looked at my eyes that looked ok, and reapplied lipstick thickly.
Returning to the living room, I stumbled as I saw him sitting on the couch naked except for the short white socks, slowly stroking his uncircumcised but still soft cock. It jutted up from a mass of black pubic hair over large testicles.
"Is this what you wanted, honey?" he asked me and, though my throat had constricted to almost nothing, I squeezed out a yes.
I walked across the room nervously, forgetting how I was dressed completely, but staring at the flopping mass between his slightly spread legs. Honestly, I had never seen an uncircumcised cock. I suppose, even as a feminized guy, I shouldn't have been so fascinated with it. But I was anyway.
"Come and look then, honey," he said as if he was reading my mind. Still not hard, he let go of it and it dropped between his legs. He'd said he wasn't particularly big but I wondered if his idea of big was the same as mine. As it was, it wasn't very big around but even soft and completely hooded still, it was almost touching the seat of the couch between his legs.
I guess I proved how fascinated I really was as I found myself on my knees as he spread his wider. His hands rested on his thighs as I stared at it. Carefully, I took it in one hand, holding it more upright and seeing the heavy, disproportionately large balls dangling loosely beneath it.
Though starting to harden a little, the cock in my fingers was still soggy soft and sheathed. Truly interested, I moved the sheath back and saw essentially the same thing I saw when I looked at my own. Maybe this way the head was a little more flared than mine but not much thicker.
Impulsively, I rose a little further onto my knees and took the entire soft mass into my mouth.
"Oh god," he gasped and stiffened. Soft, it was entirely inside my mouth with my lips around the base as my fingers explored the unbelievably large balls. His body stiffened, his thighs vibrating, as I licked at the mass in my mouth. He moaned and made incomprehensible sounds. Slowly, it hardened, unfolding itself and forcing me further up on him until my tongue could trace the shape of the unsheathed head with about half of its length outside my lips.
Sitting back again and taking it in my hand, I now had a full view of it hard. The head, that could still be partially sheathed in loose skin when I moved my hand up far enough, was half again as large as the shaft at the flared lower edge. At the same time, it was unusually long from the pointed tip to the flare. The shaft wasn't much thicker than mine but, hard, curved up toward his stomach and was at least 7 inches - at least 2 inches longer than mine.
When I put my mouth back over the tip, his hands went to the back of my head and pressed down. I forced myself back away and looked up at him.
"You can pet my hair or do whatever to my shoulders, but please don't push me down on it. I have to get used to it on my own, okay?" I asked. He nodded.
Again, I put my mouth over the flared head and used my tongue to stimulate it as my hand moved the loose skin up and down along his shaft. The texture of it was different from anything I could remember, the taste was neutral but just slightly slippery, and the smell was unlike anything I could remember. None of it was the least unpleasant. To get a better angle, I turned my head down and put my hands on his hips. Sucking, I could move down his length until it touched the back of my mouth before moving back up to the tip.
"Oh, baby! Oh, honey! Don't stop! God!" he moaned as his center moved up and down to fuck my mouth.
I took it in my hand, stroking it, and sat back away slightly.
"Is this the way you want to cum first?" I asked him.
"Oh yeah, baby! I'll do anything if you'll finish it," he moaned.
"You're not going to be all done, are you?"
"Not even close," he said with a chuckle.
I wasn't sure I wanted him to cum in my mouth but it was sort of an "in for a dime, in for a dollar" kind of thing. What the fuck! I might as well do it all if I was going to do any of it.
Knowing better than any woman what feels the best, I gently massaged his big balls as I stroked his length and sucked on the tip, moving up and down over the top half of his length. I moved my hand around it faster than I moved my head up and down and was rewarded with his moans and hunching and groans. Careful to accommodate me, his hands roughly massaged my shoulders with an occasional stop at the back of my neck. He obviously didn't trust himself to stroke my hair.
"Oh! Oh! Oh! Ahhhhhh!" came out of his mouth as he tensed and shot into my mouth.
My first inclination was to gag and be violently ill with the mass of fluid that filled my mouth and, I'm sure, I did somewhat because quite a lot coated my hand on his shaft. But then I really sucked on it and swallowed what I sucked out of it. The initial shot had been too much but after that it wasn't bad. In fact, it tasted pretty good even if it was just the slightest bit bitter.
Frozen for a moment, one of his hands squeezed my shoulder almost painfully while the other stroked my hair as he hadn't dared before. Licking a little, I finished sucking him dry and trying to clean up some of the mess. Sitting back, I licked his cum off my hand where I'd lost it at first. He looked at me through unnaturally shiny eyes and moaned as he saw me do that.
"I guess you liked it ok, huh?" I asked and he smiled broadly.
"Oh yeah. That was the best."
He chuckled.
"Give me a second to catch my breath and I'll show you how good it was." I got up, sat down on the couch next to him, and let him gently hug me as I tried to be at least moderately ladylike, pulling the skirt down as far as it would go, and crossing my legs at the knees.
For quite a while, he lounged back on the couch with his arms up around his head on the back, his legs spread about as far as when I was between them, and my hand explored the hair of his thigh. For a moment, I wondered if he'd fallen asleep. But, as I became truly concerned that he had fallen asleep, he threw his arms forward in an exaggerated effort to get up that took him to his feet in an almost startling hurry.
"Ready?" he said as he reached for my hand. I wasn't sure "ready" for what but didn't care. He'd said it was my turn. As I got up with his help, he twisted and put his hand behind my knees, lifting me into his arms. I'd once tried that with a girl and, though I'd succeeded, it had practically killed me. As I quickly wrapped my arms around his neck to keep from being dropped, he effortlessly carried me across the room, into the hallway, and (I blushed) into my bedroom.
"Lubricant, honey?"
"Uh yeah. In the night stand," I said, twisting in his arms to look toward it. He nodded and very gently sat me down on the edge of the bed.
It didn't take him more than seconds to find the lubricant. I just watched as he took it from the drawer and sat it down on the bed next to me. Kneeling down in front of my modestly crossed knees, he looked into my eyes and grinned.
"You're going to like this a lot. Promise," he said softly. "Now. You're not going to take anything but your panties off. Do you want to do it or do you want me to?" I loved his smile.
Honestly, I want to admit I was completely undecided and, because of that, didn't move. It wasn't like an earthshattering decision. I just didn't want to make it. He nodded, smiled, and leaned forward. His hands went along the outsides of my thighs under the skirt and found the flimsy waistband of my panties.
I didn't really help him as he got a firm grip on the nylon until his hands went to my bottom, pushing the panties down as far as possible while I sat on them. I lifted slightly, expecting him to pull the panties out from under me but totally surprised when his fingers met at the top of my ass crack and very slowly moved the panties and fingers down across it until the panties were below my ass cheeks and his fingers had brushed across my anus.
I uncrossed my knees and watched him grinning as he slowly pulled the panties the rest of the way to my calves and then, more jerkily, down to my ankles. I lifted one foot so he could take the panties the rest of the way off. I was panting.
"I want you right on the edge of the bed now. Just lay back and enjoy it, okay?" I did as he suggested, laying back and letting him guide me closer to the edge. Having my feet on the floor bent my back a little uncomfortably I noticed as his hands brushed my stocking covered calves. My knees were modestly held together as his hands stroked along the sides then around to the back of my knees and back down to my ankles two, three times. All I could do was lay back, staring blindly at the ceiling and feeling the goose bumps roam up and down my legs.
When his hands went up the back of my thighs, all the feelings intensified and peripherally I noticed that I had to open my mouth to get enough air into my lungs. Almost protectively, my hands moved to the blouse covering my stomach though I wasn't protecting anything. Getting my eyes to focus, I looked down across my body and saw his smiling face as he looked back at me, his hands going up the back side of my thighs to the short skirt before his touch intensified 10 fold as the fingers touched bare skin.
The difference in the direct touch of his fingers was so great, I gasped and my eyes lost focus. To enjoy it thoroughly, I closed my eyes and lay my head back on the bed. His fingernails scraped back down across the bare skin at the sides of my thighs. Only my closed legs kept my hardness from tenting up the skirt now.
The cooler air of the room notified me that his hands had lifted the sides of the skirt before moving downward, back up the fronts of my thighs, down onto the stockings, up, down to the tops of the stockings, up. I knew then that the skirt was bunched at my waist.
"That's so cute," he said breathily. "It looks like a pussy that way. Mmmm. A shaved pussy." Embarrassed and very nervous, muscles vibrated through me. I gasped and sucked for air as I felt him kiss at the very conjunction of my legs, to the top of the base of my hidden cock. Three more kisses had similar effects at the conjunction of each thigh to the sides then the top of my pubic area.
"Now I want to see it. I want to see your little clit. Your clit and your pussy. Let me see now." His voice was a whisper. Barely more than a sigh. I opened my legs.
From experience, I knew then when I'd been tucked as I had been, and no matter how turned on I was, it was still mostly soft when I freed it. His soft chuckle told me that was what he saw now.
"Beautiful," he said in that same soft voice. It almost sounded worshipful. His hands moved to the insides of my knees, pushing them wider until I was forced to move my feet further apart. "That's it, honey. Show me."
His fingers edged up to the insides of my thighs at the tops of the stockings and made me shiver with anticipation of his actually touching me. I knew he was going to but I didn't expect it at all when he took my cock completely into his wet mouth. Though I didn't immediately recognize it, my reaction was to raise my legs and spread them even wider as I loudly gasped with pleasure.
His mouth wetly left me as he sat back and lifted my comparatively tiny testicles. I cringed as his finger brushed across my anus.
"What a darling little pussy," he said. The word "darling" had never crossed my mind and particularly in association with what he was so softly touching. He explored that part of me that had never been touched directly by anyone but a doctor (then with rubber gloves) but went on talking in that almost worshipful voice. "We'll have to thoroughly explore this, of course, but I think we have to drain the first needs first so we can spend a little time."
The way his finger brushed so gently over my tiny tight opening and the wild feelings that roared through my head didn't allow me to grasp what he was saying at all. If I'd actually been listening to myself, I might have been embarrassed by the whimpering and little squeals.
His finger, joined by a couple more, stroked along my ass crack lightly as I felt his tongue lapping at my tightly drawn up balls that seemed to want to crawl up inside me. Totally outside the raging feelings of what he was doing, I could feel the wet tongue contacting the individual pubic hairs that I couldn't shave off as I had those on my tummy higher. Each hair seemed to be a tiny trigger to its own personalized set of nerves.
Completely hard now, the way my cock jumped off my shaved stomach with each triggered reaction was a little distracting from my feeling completely female but I forgot it completely as he sighed, "I love eating pussy," and moved his tongue's attentions to my sensitive anus.
Using just the tip, he teased it. I felt as well as heard his wet his tongue before returning it to the closed opening of my body. I could only squirm as his fingers held my scrotum up out of his way while he tickled the bunched muscle. His breath caressed through the hairs there that I couldn't see but could certainly feel.
I heard myself whimper as I bent my knees and drew them very close to my chest. Incongruously, I hoped I wouldn't inadvertently kick him with one of the high heels that hovered near the points of his shoulders. Certainly it would have happened when I felt his tongue harden and press like a tiny cock into the opening. I know I squealed.
"Ohhhhh!" escaped me as his tongue opened me more and continued to explore. His hand was holding my bounding cock against my skin as well as holding my testicles out of his way. The touch of his lips in a wet kiss - a french kiss - made me arch again. I tried to relax the tight muscle for him as his teeth touched the sensitive skin. The tongue continued to probe while all I could do was gasp and sigh and squirm under his ministrations. The reactions to his long exploration of me that way were slow enough that I almost didn't hear his comment for the blood surging through my ears.
"I'm going to finger fuck you while I lick your little clitty," he said. His mouth away from me, I felt his finger in a slick moistness across the tight pucker but it didn't register somehow. "Just relax." My guess is that he moved the finger away from me to apply more of the lubricant but I truly didn't notice at the time. Then it was pressed against the tiny, unused opening.
I stared at the red and black of the inside of my eyelids as my total concentration went to what he was touching with the tip of his finger. I didn't know that he was splitting his concentration between the finger and its goal with looking up my feminized and sluttily available body.
I clearly felt the tip of his finger open and slide into me. Maybe it was a fractional inch and maybe it was to the first knuckle before it twisted to one side and then the other. I held my breath.
However much was in me, it retreated (I'm sure to gather more lubricant) and re-entered until I felt the skin stretching as a drier part of his finger pulled at it.
Though I wasn't thinking about it at all, I should say that I have a small butt plug that I've had all the way in me a few times as well as having sat on a beer bottle twice at the suggestion of people I was chatting with on-line. Being opened that way was not an unpleasant experience even under those cold conditions, but there were three major differences. Unlike those things, his finger was warm and, in a way, not as noticeable. It was also rougher than the smooth surfaces of glass or plastic. And finally no bottle or plug moved inside independently.
I squealed again as he moved the tip inside me slightly.
Then he began slowly twisting it from side to side while pressing in, pulling back, pressing in, and pulling back. I felt the fingers on either side of it contact the skin outside as he squirmed the middle finger around my insides to feel everything.
"That's it, honey. Love it," he whispered as he fingered me. Used to the feel of it then, I felt disappointment as he stopped moving it in me and slowly pulled it back to the entrance. I gulped at a total lack of saliva in my panting mouth as he paused with it just inside me. I'm sure now that he was adding an even more considerable amount of lubricant for the second before I felt him press inward again. A considerable increase in pressure - not really pain - told me that he was sliding a second finger into me beside the first.
Twisting and turning the combined mass, he moved them further and further into me until I once again felt his knuckle against the skin outside. At once, I felt his thumb stroking or pinching the flesh between my legs against the embedded fingers as the fingers spread and curled and stroked at my prostate. This wasn't anything like a doctor's examination and sent zinging assaults of almost untouched nerves every bit as sensitive as those in the head of my cock or anywhere else on my body. Maybe there are nerves that register pain to a greater extent than these deeply buried ones, but I don't know of any that could rival registered pleasure and clearly and completely.
I felt his lips take the tip of my cock - my clitty - and his busy tongue moved on it even as his fingers began squirming and moving in and out of my ... pussy. I'm sure the way my body humped instinctively would have been a real turn-on looked at from outside but honestly I didn't notice it. My entire body was reacting to the combination of his fingers fucking me and his lips and tongue moving on my clit.
I didn't have any warning from my body as, simultaneously, it clenched, everything behind my eyelids turned to flames, and the most wonderful of all feelings slammed through my lower body.
Some indeterminate time later, I heard his lips smacking wetly as he sucked hard on my cock tip, his fingers still moving gently in and out of my ass.
My eyes almost stuck together with wetness, my body relaxed from the wild orgasm and I looked down my body to see my splayed knees and the high heels resting on his back, nearly touching.
He didn't stop what he was doing, though the movements had slowed considerably, as my shaky hand went to the back of his soft hair.
"You liked that," he said unnecessarily as I closed my eyes and laid my weak head back onto the bed.
"Mmmm," I mumbled, the answer obvious but beyond me. Still inside me, his fingers squirmed while his other hand moved thumb and two fingers to my softening cock to stroke me slowly.
"I think we're both ready now," he said. "Thanks to how hot you are, I'm ready for sure. And I think you'll be able to last, too."
I took a deep shuddering breath and slowly sighed it back out. At that moment, I couldn't have cared less what he was talking about. In fact, I'm sure I didn't know what he was talking about or even pass it through my slowly churning mind. He chuckled at my obvious never-never land attitude.
"Well, I'd love to feel those sweet breasts against me." Breast forms actually. "And I want to kiss you. But I think the first time, it might be better from behind. So the only question is whether you're limber enough to lay flat or if you want to be on your knees."
Responding in deep way that really didn't involve my thought processes to the extent they should have been involved, I lifted one foot off his shoulder and turned to the side. I would have been totally content to just fall asleep like that. Maybe a nap.
Far off, I heard him apply the lubricant to himself though I wasn't thinking clearly enough to recognize the sound or care.
Like some kind of doll, he lifted me with hands on my waist. The extent of my help was to turn one shoulder so my body was straight, my head turned and laying against the coverlet.
I felt him touching and rubbing my ass crack but really didn't care at that moment. If he wanted to finger me, it was more than all right with me. I'd enjoyed what he'd done to me and was ready to at least passively accept what came next. I wasn't thinking well at all.
Of course I felt him press against that opening he'd so recently explored. Somehow, I knew what he was doing. I just wasn't reacting. Not hindering in the least, I certainly wasn't helping. His hand steadied my hip, the other doing ... something else. Of course, what it was doing was guiding his considerable hardness to my little open, relaxed hole.
His other hand went to my other hip, holding me in place, as I felt him slowly but very steadily opening me. The feeling increased from a touch to the gentle intrusion his fingers had showed me to something entirely different. In fact, it edged slowly toward an almost panic filled pain. Even as my mouth came open and the sparkles before my wide opened eyes turned red, it popped into me. I squeaked.
"That's it, baby. That's the hard part. It's okay now." I could feel his body and his hands vibrating as he paused. But, as I gasped for air again, he pressed forward and some of the pain returned.
"Good, honey. That's it, baby," he chanted as he moved in and out slowly. More in than out. "Oh yeah. Good." My body rocked back and forth with his push further into me, moaning.
"Uh," I heard from myself as his hard cock contacted something very deep inside me. I cringed away from it though it didn't quite hurt. Just uncomfortable. In response, I thought, he pulled it much of the way back out before, equally slowly, pressing forward to the same point again. I could feel his pubic hair tickling the back of my thighs.
"That's it, baby. Take it all," he said. "You love it don't you?" he continued with a chuckle. I didn't answer but I did love it.
The feeling was far beyond anything in my experience. One second, as he quickened his movements slightly, it contacted that furthest extent uncomfortably before the flared head dragged across all parts of my prostate and out almost to my spread opening. Cringing away from that uncomfortable furthest extent, I soon found myself pressed against the bed, his weight on my back and mouth close behind my ear, panting with me.
Now his chest, supported on elbows, pressed against my back while his middle humped up and back into me. He was moaning against my ear in time with his strokes as both quickened.
"Oh, fuck," he said in a sigh. "Uh uh uhhhhhhh."
His body tightened and I felt him lengthen unbelievably into me. Hot. And realized he'd cum inside me.
After a moment of spasming orgasm, he stroked again in and out of me slowly, draining himself into my depths with a grunt at each stop.
I'm sure I stayed there on my stomach in that compromised position longer than necessary. I really was in that blue wonderland of afterglow that had absolutely nothing to do with my feelings for the guy who was draining his bladder in the bathroom nearby or any consideration of continuity.
Actually, though it was nice of him, it didn't affect me much when he dressed as I drained out a consider amount of fluids on my own in the bathroom or that he stopped at the front door on our way back through the house, obviously ready to leave. Pleased that he wanted to, I accepted his arms around me, the gentle stroking of my back and skirt covered bottom, and several long, lingering kisses that didn't contain the same sexual connotations as the earlier ones. I liked his compliments of how I still looked, interspersed with kisses, and how good our love making had been.
Alone again, I relished the tingling of my ass and need to return to the bathroom a couple of times, the memories of the evening's activities, and his tentative promises of a rematch at some undetermined time in the future. Did I want to do it again? Sure. Did I want to do it with him? Sure. He'd been good. How would I feel if I never saw him again? Let's say neutral. If it happened again, good. If it didn't, that was fine too.
Whatever happened in the future, I'd still have the feelings.