From Top to Bottom 2: Getting to Know You

story continued from part one

Chapter Two – Getting to Know You

Two more weeks went by, and we met each Saturday, got a room and pleasured ourselves, sometimes masked and sometimes not. We were now very comfortable with each other and our roles. We did pretty well everything we could, me only passing on the “buggeree” role. Ryan made no big deal of this, just laughing and saying I didn’t know what I was missing, and don’t knock it till you have tried it, and so on. But I could see that he was maybe a bit frustrated with it.

And it was me who decided to move on the next level. I invited him to my place on the following Saturday, instead of the club. This was quite a big deal, for me. I am a private person, and I live a quiet life, ordered, with all my friends nicely compartmentalised. Aside from all the fucking and sucking at the club my life is quite conservative, but my pervy side is generally kept separate. Ryan wouldn’t be the first to see my place, not at all, but I wanted it to be just right.

I have quite a bit of rubber there, but generally take it to the club and change there, although I like to dress up and relax around the apartment. I am lucky it is on the top floor, the only suite there, so my privacy is guaranteed. I love rubber and wearing in a non-sexual setting still gives me a buzz. We agreed we could have some rubber fun, and I told him he could bring any clothes or other goodies he liked. His eyes lit up and I knew we would be having a really good night ahead.

On the night, I was surprised to find myself rather nervous, I can’t think why as I was perhaps 8 to 10 years older than my partner and I consider myself a person who is pretty cool under stress, but I was still a bit jittery, but also very excited.

When he arrived and I buzzed him up, I almost lost my breath. From top of head to tip of toe he was in black latex. I don’t know how he had dressed like that, in the elevator? A full, hooded cape covered his head and extended down to his ankles, where his high heeled boots peeked out. The cape had slits at the sides through which his arms and gloved hands extended as he embraced me. I breathed in the heavy musk of rubber as I kissed him under the hood. By his side there was a large leather bag, and I smiled while I thought of what might be in it.

“You like?” he asked as I led him inside.

“Oh god, yes, let’s see what is underneath. Did you drive here like that, sheez?” I could hardly wait for the cape to come off.

“Of course, anyone stops me I say I’m going to a Fetish Ball, the cops are pretty cool with that now. You look really good too, and without the mask, lovely.” I had a burgundy full body catsuit with black stripes down the arms and legs, one of my favourites. It was drum tight and a bugger to get into (and out of) but once in it the feeling is fantastic. Ryan looked a bit nervous, even sheepish as he said.

“I know you’ve gone out on a limb for me and I really appreciate coming up here. Now I’m a bit nervous that I might have gone over the top, I have some other stuff in the bag but if you’re not into this.” And he began to pull the press studs of the cape apart.

“Ryan, don’t worry, I’m just very happy you could come, just relax.” And as he pulled the cape off his shoulders I could see what he was referring to.

“I don’t know if you are into this, I like dressing up sometimes, you okay with this? I can change.” I could see he was perhaps a little tense, but there really was no need to be. The cape dropped to the floor, and he stood there.

The perfect rubber tranny!

“I don’t do it all the time, just special… well… occasions like this.”

“And I’m touched that you did.” And I took him in my arms and we held each other for a couple of minutes. I felt his silicon boobs pressing against my chest. I stepped back.

“Let me see you now, hhmm you are a beauty.” And he was. He had a white blouse with loose sleeves tucked into black wrist length gloves. It had a high frilled collar and buttons at the front. A short black flared skirt extended down to mid thigh, covering either black tights or stockings I couldn’t tell… yet. Extending from hips to under his “bust” was a tight black and white striped corset, pulling him into maybe 28 inches or so, which was pretty good. His feet were in laced granny boots with 5 inch heels and he seemed to have no problem keeping his balance. Naughtily he raised the hem of his skirt, exposing stocking tops, suspenders, black panties, frilled with white. I could see the outline of his cock through the rubber, straining to be released.

“You look a bit uncomfortable there.” I laughed.

“Oh, I’ll be fine, the discipline will do me good, makes the reward later on all the more pleasurable.” I could only agree. He placed his gloved hands on his prominent boobs.

“These are top quality silicon; I think they look pretty good, don’t you?”

“Oh yes, but it’s what is underneath that I want to get my hands on.”

“I have a full head female mask in the bag, if you like. It’s skin coloured with red edging around the lips and blue eyes. It’s a perfect mannequin mask. I didn’t wear it on the way here, didn’t want to get arrested, ha ha. Not that I care. Would you…”

“Yes, I’d like that, beautiful though you are, it does look a bit incongruous, your male head on that body.” He laughed and quickly got the mask from his bag, and deftly slipped it over his head. It was a tight fit but I helped him tuck in his hair and then tucked the collar under the collar of the blouse. He was a perfect vision in black and white.

I haven’t dressed as a rubber tranny myself, and it certainly has crossed my mind over the years, despite being a top, as noted before I have fucked them. I do like the whole incongruity of it; a pretty (or masked) face atop a (possibly) hourglass figure, slim legs, high heels, pert boobs, and under the skirt….a nice hard cock. A cute rubber tranny just pleading to be sucked and fucked, what could be more fun than that?

“I know you love masks, and this one I bought with you in m….” I quickly took his masked head in my hands and kissed him tenderly through the red rubber lips, holding him close.

“Let’s eat first, there’s lots to do.” The meal was light, with some dry white wine and a light dessert. It was clear that both of us were waiting for it to end, so the proceedings could begin. We made pleasant conversation, him saying nice things about the apartment, and how private it was. I showed him around, and showed him the latex sheets on my bed, a special occasion, I said, and he smiled through his mask. This, I thought, was going well. He helped me clear away, brushing against me, flirting, swishing his skirt. I wanted to fuck him right there, him pinned over the dining table, but held back, we had all night. He had a beautiful face, but the mask was a stunner too, and I couldn’t help taking his head in my hands again and drawing him to me.

“So where will it be, bedroom, living, over the kitchen table, ha ha.”

“I saw the sheets and pillowcases on the bed, well, where else? So are you ready to deflower a mischievous rubber tranny?” He laughed. Oh yes, I most certainly was, and took his hand as we went to my bedroom.

He lay back coquettishly on the rubber covered bed, then raised the hem of his skirt, exposing his frilly black and white panties. I placed myself comfortably between his legs and bent over, fixing my eyes on the pronounced outlines of his cock and balls, now hard and straining the rubber. I laid my face on the taut rubber, drawing in a big pungent breath, nudging his cock with my nose, licking the rubber. I placed a hand on his cock, as if testing a ripe plum ready for eating, and he certainly was.

His cock was lying sideways and so I pulled open the top of his panties and the purple head popped up, a little pre-cum oozing out. He was ready to come, so I had to slow down, and I trapped the shaft of his cock with the frilly top of his panties, and it looked so cute, the purple head peaking out. I licked the pre-cum off and fondled his balls through the tight rubber encasement. I moved sideways and across him, zipping down the fly of my red and black catsuit. My hard cock sprang out and he grabbed it with both hands and steered it to his mouth hungrily. I had a feeling that this first encounter in my bed would not last long, so I released his cock from the panties and taking a deep breath, swallowed him straight away to the hilt.

Within a couple of minutes it was all over, far too quickly, we were like two first-timers, but we were hungry for each other and we had the night ahead, so after a rest I got up and returned with a couple of glasses of wine, and we lay in the semi-dark sipping and talking. He was very noncommittal about his private life, I would have liked to know more, but didn’t press. He made a few jokes about me being an anal virgin, and how he would be honoured, thrilled to be the one to crack my virgin bottom. We laughed but I was not to be drawn on that, yet anyway. He had pulled his panties back up and my hand was underneath gently squeezing his shaft and tickling his balls. He was young and very fit and I knew it wouldn’t be long before he was ready for more.

I have been with rubber trannies lots of times before and it is a strange sensation lying next to a rubber dolly, with her boobs facing skyward. Fondling them is an odd feeling, I’m not fooled it’s a woman, I don’t want it to be a woman, but I love the idea that under the rubber carapace there is a handsome young man with a lively receptive cock.

Eventually he said he was aching for me to fuck him hard, and I was certainly eager to please. I asked him if he didn’t mind a bit of bondage, and after only a very short pause he said okay. So I instructed him to turn over on his stomach, and as I had prepared for this, gently tied his wrists to either side of the headboard with two thin pieces of rope. He now seemed a bit nervous as he knelt back, spreading his legs.

“I’m going to be alright aren’t I? I feel very helpless here.” But somehow he didn’t really act helpless, it seemed a bit of an act, for my benefit as a “top” perhaps.

“Don’t fret, you’re in experienced hands and you will love this, I promise.” I gingerly pulled down his panties, wet with his pre-cum on the inside, exposing his cock and balls, and his pouting rosebud. From my bedside drawer I pulled on surgical gloves and a condom, taking my time, listening to his hard breathing, then applied some lube to my cock. I placed some on my first two fingers and pressed them to his sphincter. He shivered.

“Ooh, that’s cold.”

“Don’t worry, I’ll soon warm you up.” I laughed, and Ryan did too. I gripped him firmly by his narrow waist and heard him take in a breath. Then I pressed the head against his hole and waited while he relaxed, then pressed again and the head of my cock plopped into him. He let out a few aaahhhs, quite loud - which gave me an idea, and I grabbed his wet rubber panties lying on the sheet next to me.

“I don’t want the neighbours calling the cops with all this noise, so I’m going to have to quieten you down. Open your mouth, now.” I said quite sternly. He peered back and saw me folding his latex panties into a tight ball, with the wet side out.

“Oh no, you can’t, look I’ll be quiet, please…” But with him speared on my cock it was easy to pull his rubber head back by placing my hand over his forehand, and so his natural inclination was to open his mouth and then - not too tenderly I stuffed the tight rubber ball into his mouth.

“Aaaarrgh, mmmmff.” He moved his head from side to side, but with my two hands at work and him impaled on my cock and unable to use his hands it was easy to push the damp ball in until only a small black portion could be seen between his rubber lips. He looked lovely, so vulnerable, as he groaned in defeat.

“Relax, relax, this will be fun, now you can buck and scream to your heart’s content, breathe easy now.” And he soon quietened down as I pressed my hard cock further into him. I rolled a second pillow under his head for support and he now laid his head on it, trying to relax as I now pushed into him, up to the hilt. This was a wonderful sensation for me now, a beautiful rubber submissive – thoroughly gagged and plugged - in my control, and so I went to work, slow in and out, then a bit faster, then slower again, and at the same time felt under him and gripped his cock, which I was very pleased to see was rock hard now. His eyes were closed as he was breathing hard, moaning quietly, and I could now see with pleasure.

He had a gorgeous stretched hole that gripped me powerfully. For me it was just a perfect fit. I gripped his ball sac, trying to hold him back from coming, I wanted to do it in unison, and I wanted this to go on for a good while longer. A couple of times I simply stopped, embedded within him as I leant over whispering my feelings to him. By now he was completely at ease, I could see his eyes closed behind the rubber mask, and he mmmmfed quiet moans of pleasure.

“Do you want me to come now?” I whispered, my head gently placed on his masked head. No, he shook his head briskly, good, well that was just fine by me. And so we proceeded like this for as long as I could, stopping when I was on the edge, lowering my heart rate and then back again. Then with a whispered, “okay, ready?” and a mmmffed nod from Ryan we conjured a joint orgasm, me pulling him onto me to my root and wanking him hard, and he coming over the latex sheet – well being latex it could be cleaned quickly. 

It had been as good as I have ever had and I slowly pulled out of him, released his bonds and then gingerly pulled his soaked panties from his mouth. I rose and with a paper towel cleaned the bed and then lay next to him, noticing that he had already returned his panties to their right location. Nothing was said for a while as we lay together staring at the ceiling. He seemed deep in thought, and so was I and I turned on my side to look at him in profile, his handsome features still covered by the skin coloured female mask. I slipped my hand under his short skirt and rested it over his cock, now back behind the rubber panties. He smiled at last as I landed a goodnight kiss on his cheek.

Through the night he was quite restless, it was the first full night we had slept together so I didn’t know if this was normal for him or because we were together. But to reassure him I pulled him to me and we made spoons, my arm over him and my head in the nape of his neck, breathing in his aroma mixed with rubber. Finally he rested.

I awoke later to see him by me and looking, almost inspecting me with a distant smile on his face.

“Now, lover,” he placed his gloved hand on my cheek, “is there any chance of me reciprocating your wonderful attentions of last night? Don, I would love, just go wild if you would let me fuck you, for your first time, please?”

So here we were again. Why I kept backing off I don’t know, for here was a man, although it was early days, who could possibly be “the one”.

“Ryan please, give me time, it will come I’m sure, but call me a control freak, or anal (I chuckled) but I still have to be the top, I’m sorry, but I just can’t get to that point yet, I will try I promise.” I could see the disappointment in his eyes and he smiled bravely.

“Okay, okay,” and he looked at me very seriously, “but I have made up my mind that it would be the last time I ask.” That sounded a bit worrisome, so I tried to calm the moment.

“Don’t worry, I will tell you when.” I said but I knew it sounded hollow. We rested for a while longer, saying nothing, my hand resting over his panties, but the elephant was definitely in the room. After maybe an hour, with the sun now up he got up and went to the kitchen, returning a few minutes later with two glasses of juice.

“Here, we are both very dehydrated, get this down you.” He wasn’t brusque, but just a touch standoffish, nonetheless I gulped down the drink while he, very sexily and knowingly, adjusted his rubber stockings standing over me, then saucily pulled his skirt down. I patted the bed.

“Here, please lie here for a while.” And he lay next to me as I drifted back to sleep, it had been a long night, was my last thought.

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01.12.15