The Only Difference is the 'S'.

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Otazel
Otazel
2,593 Followers

Then I felt her fingers move away to rest briefly around the shaft of my cock as she took it deeper into her mouth for a couple of strokes, before returning to my arse. My immediate thought was that she needed to change the position of her mouth on my shaft, but then I felt the wetness of her fingertip slipping into my anus through the security of my sphincter, and then I realised that she had merely gone to collect saliva for use as a lubricant.

I'd never had a finger in my rectum before, in fact I'd always considered my arse to be strictly no entry, but the feeling was extremely stimulating and highly erotic. The feel of her finger sliding in and out of my hole combined with her mouth pumping up and down my cock was having its effect, and that marvellous sensation of cum collecting like a geyser about to erupt was already starting. I hate to admit it, but I loved that finger in my arse.

As you can imagine, it occurred to me to return the favour and to penetrate Sam's arse with my own finger, especially if I could time it so that my finger went in just as I shot my load into her mouth. I figured that would give her one hell of a kick, and me too for that matter, though it's probably not something I would have considered doing if I wasn't already high on sex.

I tried to wiggle my finger into her sphincter, ready for a one push entry as I came, but her anus was dry and tight, and I couldn't get my finger to go in. Obviously I needed some lubrication, but saliva wasn't an option and whatever I used would have to be quick, because my climax was rapidly approaching and I'd soon miss my chance. Then I realised that my fingertip was less than an inch away from the best source of lubrication available, her pussy. All I had to do was stretch that little bit further, dip my finger into her vagina and then back into her rectum. Then she could feel the pleasure that her wriggling finger was giving me.

Timing was now getting to be urgent, I was on the verge of cumming. It wouldn't take more than a couple more thrusts of her finger into my arse and another quick swirl of her tongue around my cock and I'd be filling her mouth with cum whether my finger was in her arse or not.

I know this may sound silly, but penetrating her anus as I came had become a big deal for me. I'd never had my arse played with before and the stimulation it brought was overwhelming me, and I dearly wanted Sam to experience that same pleasure, even though in hindsight she'd probably already tried in numerous times before.

I wriggled in my seat and stretched sideways, trying to reach under her panties and around past her arse to her pussy while at the same time trying desperately to hold back my climax. I managed to get maybe an inch past her anus, but I hadn't yet reached her pussy, then I stretched a little further, my cock twitching in readiness to explode, ands still I couldn't find that honeypot of hers. She rammed her finger deep into me, sucking hard on my cock at the same time, and that was it, I couldn't hold back any more and my spunk began to spurt into her mouth.

Still trying to reach my goal and penetrate her before I'd finished, I lurched to the side, almost pushing her head away from my cock as I struggled to get my finger wet in her vagina. But even though this lurch gave me an extra inch or so of reach there was still no sign of her pussy, just the soft loose skin that lay between.

Then the terrible truth dawned even as my cock spewed cum into her mouth, there shouldn't be loose skin between anus and vagina and the reason I couldn't find Sam's pussy was because she didn't have one. Sam was a man, and I was exploring the back of his scrotum.

I went into a blue funk, a complete panic not knowing what to do. I still had his finger buried in my arse, and I was still spurting cum into his mouth. Nothing had actually changed from me unreservedly enjoying what was happening to now when I felt sick to my stomach; except that I now knew the girl I was with was in fact a male. I couldn't get my head around it. My body still said that it felt good, but my mind was in a turmoil and suffering from shock. In the end I pulled his hand away from my arse shuffled as far into the corner of my seat as I could and pushed him into the passenger seat, my cum still trickling from a fast disappearing erection.

"You're a fucking man." I told him, as if he didn't know.

"I wasn't sure, but I thought you realised." He replied, looking nearly as shocked at my actions as I was at my discovery.

"Get out!" I shouted for him to go, and then watched in disgust and repugnance as he scrambled from the car and made a run for his door; tottering as only a man can on high heels.

How had I never known?

As soon as he was out of sight I opened my car door and emptied my stomach into the roadway.

My mood on the drive back home alternated between bitter anger and deep self loathing, with a good dose of betrayal thrown into the mix. Why had he not made it clear? But then I could see all the clues had been there. The heavy makeup, the boyish build, the reluctance to let me touch him and his hesitation before touching me, all should have pointed me in the right direction. And at least he had had the decency to hesitate.

I lay in bed that night trying to come to terms with what had happened and trying to make myself feel good about it. I didn't want to carry guilt for having enjoyed the touch of another man, even though I was unaware of the fact at the time. But nor could I deny that what Sam and I had done had felt really good, and even now my cock twitched in approval when I thought of his mouth gliding up and down its length.

Round and round went my mind, always condemning him, but then seeing reason and forgiving him. I tried to make myself hate him, but I couldn't, nor could I hate myself for enjoying our times together. We had, after all only ever kissed and cuddled, apart from the oral sex that he was so damn good at. Could I cope with having kissed a man so passionately? Of course I could, a mouth is just a mouth after all, and a tongue is only a tongue, and it was nice to have another human being in my arms again.

I was, I realised eventually, justifying my feelings and telling myself that I'd done nothing to be ashamed of, nothing that I couldn't look back on with a wry grin and a fond memory. I was also telling myself that it was alright to have kissed a man and to have enjoyed oral sex with him, and maybe I was also subconsciously preparing myself for the logical next step, that if it was alright in the past, then it would be alright in the future. I decided I would meet Sam again, but this time with no pretences.

The next night there was no sign of Sam at the bus stop, and I fell back into a confusion of emotions. Should I let things lie as they were and remember a short interlude of intense, if mistaken, enjoyment, or should I seek him out, and if I sought him out, would it be just to apologise for my homophobia, or to take him back into my arms once more. Why couldn't life be simple?

It was two nights after that when Sam next stood waiting for his bus, still dressed in skimpy female attire and still wearing a pound and a half of makeup. I pulled up alongside and opened the door, but he didn't get in. Instead he bent down and looked warily at me before asking.

"You're not going to hurt me, are you?"

I shook my head silently and motioned for him to get in.

We sat in silence as we drove home, Sam casting quick nervous glances in my direction every time I moved to change gear or adjust the radio. I hadn't given any thought to how I was going to handle this, and the silence was wearing at my nerves. In the end I decided to chance my arm. I reached out and placed my hand gently on his bare thigh, as high up as his skirt would let me.

He looked at me quickly in surprise and then fixed his eyes on the road ahead. But he didn't place a restraining hand over mine, in fact he slid down into his seat, revealing more bare thigh before slowly but deliberately letting his leg fall open towards me. For the rest of the journey I stroked his thigh, letting my hand wander along its full length, from knee to groin, stopping only when I felt the flimsy material of his panties brush against the side of my fingers. I made no attempt to touch him intimately even though the desire was there, and I'm sure he would have let me because all the time I stroked his thigh he made no objection, he just kept his legs wide apart in unspoken consent. By the time we pulled up outside his door we were both breathing just a little heavier, and I was sporting an erection.

I wanted things to go further but wasn't sure now if I should take the initiative and kiss him or let him come to me as he had done at the start, but in the event neither course applied.

"Would you like to come in?" He asked quietly, looking at me before adding. "It doesn't matter now that I'm sure you know what I am."

"But I'm not sure what you are." I countered, telling the honest truth. "I don't know if you're transsexual, gay, or what. All I know is that someone I thought was an attractive girl turned out to be a man." My voice cracked slightly with the emotion of the statement.

"Well, I guess that I'm a gay man who likes to live like a woman. But I'm happy being a full working order male with no wish to become a real woman, and so I'm a transvestite, but not a transsexual. I'm always going to be a man."

I nodded in mute understanding. This was still the Sam that I'd grown fond of, that I wanted to have sex with, and that I enjoyed the feel of in my arms. Did the fact that 'she' had turned out to be 'he' make all that much difference? Should I no longer want him because his plumbing wasn't quite what I expected? I was still fighting the battle between my instincts and my upbringing. So far instincts were winning -- just.

"Would you like to come in, no strings attached?" He repeated his offer.

I followed him through his door like a lamb.

A few minutes later and we were standing in his lounge, nursing mugs of strong black coffee and wondering where we should go from here.

"I think I would like to know exactly what is under that get-up. Take off your clothes." It was said and meant as an instruction. I wasn't intending to be fooled again.

Sam was right, he was a full working order male, although the thick eight inch erection he had looked out of place on his skinny, boyish frame. As he stripped he revealed a smooth, soft looking body, completely devoid of body hair apart from the little nest of brown fuzz from which his cock sprouted. He was pretty much as I had imagined, supple and unmanly with a tight little bottom and long slender legs. The only surprise was that when he removed his bra he was completely flat-chested, the bra, for all its diminutive size, was padded to suggest a feminine shape. I had thought he might have silicon implants to improve the deception.

When he had finished he stood there naked, waiting for me to make the next move, but with his right hand instinctively onto holding his erection and moving in a vaguely sexual manner.

I looked at him for a minute or so and then I began to undress. I wanted to see just how far I could let myself take things, and in any case Sam had seen my cock on a number of occasions, all of them pleasurable.

We stood naked before each other, all pretence now cast aside.

"Come here and kiss me." I told him.

This was the moment as far as I was concerned. Either I would find the kiss of a man repulsive and nauseating, and that would be the end of things, or I would enjoy it as I had previously and so innocently, and we could take things from there.

We came together standing naked in his lounge, our two bodies pressed close and our arms around each other in an unrestrained clinch. For a few seconds we just stood and looked at each other, and then our mouths met, cautiously at first but then more and more passionately until we were French-kissing as we used to in the car, the only difference being that skin to skin contact now extended the full length of our bodies.

We had both gone into the clinch with solid erections, and now we could feel the two cocks touching each other and our bellies. It was an unfamiliar feeling to say the least, reminding me, as the supposedly straight guy, that I was in a homosexual embrace with a self confessed gay man. The trouble was that, far from putting me off, the fact excited me even more, letting me know that my body wanted more.

"Can we go to your bedroom?" I asked him when we broke for air.

"Yes, of course. What do you want to do?" He looked at me in part longing and part triumph. I didn't mind the triumph.

"I don't know yet. Let's just see what happens."

"Yes, of course." He repeated.

He turned and led me by the hand through into his bedroom where he stood waiting to see what I was going to do. For some reason I found his holding my hand to be very touching and not at all effeminate.

I was the inexperienced partner in this relationship, and so I gently disengaged my hand and went to lie on the bed, lying flat out with my legs a little way apart.

"Come to me. Touch me. Make things happen." I told him.

"How far should I go?"

How the hell did I know? I was new to all this, and in any case I still wasn't sure what my morals could deal with.

"Until I say stop."

That seemed to be the easiest and most truthful way to answer. After all, this was something I'd never expected to happen to me and I was still trying to come to terms with it.

I lay looking up at Sam. I gazed at his face, the femininity of his make up not looking at all out of place above his smooth womanly body, with its long slim legs, slender arms, and soft willowy torso. It was this very girly look that he had that allowed me to contemplate what we were about to do. In fact the only hard thing about him right then was his cock, a contrast that added to my excitement.

He came and climbed on the bed beside me, lying on his side so that he could look down at me, but then after a moment or two rolling on top of me with his mouth seeking mine once more.

We kissed long and hard again, not holding back, letting tongues do what they wanted, keeping our mouths locked together while we held each other tight. We ran our hand over each other's bare skin, touching and exploring. Then I felt his hand work its way south, just like mine had done many times with a woman, creeping slowly closer and closer to my crotch. He was a little bit hesitant, letting me know what he intended and waiting for my reaction before going further. I wanted his touch and the dithering was driving me mad.

"Do it. Whatever you want, do it." I let him know how I felt.

His hand now slid down, slowly still, but this time with confidence until finally he reached my cock and wrapped his fingers around my shaft, slowly stroking it up and down. I groaned with pleasure and kissed him again before opening my legs in silent temptation.

He seemed to know just what I wanted, for he moved down to cup my balls again as he had before, rolling them between his fingers and very softly stroking my perineum with the tip of his fingernail. It felt so damn good that I spread myself even further, raising my knees to allow him full access wherever he wanted to go. He took the hint and a moment later his fingertip was once again probing my sphincter, pretending to enter and then withdrawing.

I felt as if I'd reached another level of pleasure, the exquisitely erotic sensation of having my anus probed combining with the knowledge that this was not allowed, and that I shouldn't be letting a man, no matter how feminine, do this to me. But I didn't care, I loved it.

I wasn't the only one turned on by this activity, I could feel Sam's cock twitching as it lay on my hip, demanding some kind of attention if only I had the nerve to give it. All these weeks, I realised, Sam had given me pleasure with his hand and mouth, and never once had he been able to let me reciprocate, even if I had wanted to. I understood then just how frustrating it must have been. Now I did want to, I knew that before this night was over I would make him cum, if only as reward for all the times he had done so for me. My only concern was how and when. I didn't think I could suck him off, at least not this time, so it would probably have to be a standard wank, though right now I just wanted to let him play with me.

Suddenly, without warning, Sam leaned away from me, rolling onto his back and looking the other way. I thought for a moment that he had read my thoughts and done it deliberately to give me the chance to feel him, to play with his cock, and so I reached out, incredibly conscious of wrapping my hand around another man's shaft for the very first time. Sam gave a little 'mmm' of pleasure as I touched him and rested on his back, letting me have my way.

It was strange and exciting feeling to have the hard shaft of another man's cock under my fingertips. I'd touched my own erect cock thousands of times, but then every time I was conscious of the sensation in my cock rather than the sensation in my fingers. This time there was no cock sensation to cover up how it felt to my hand, and it felt good. Sam's cock was quite large for such a skinny guy, and I could feel it, hot, smooth and hard in my hand. Somehow it also gave the impression of having a life of its own, I could feel little pulses and jerks from it, as I explored its length and ran my fingertips over its head. Sam grunted again, but I'm not sure who was getting the most pleasure, him or me.

"That's good." He smiled at me, triggering a wave of satisfaction that I'd got it right first go.

"But just wait a sec'" He looked apologetic for stopping me.

Letting me touch him had not been his original purpose in rolling away from me, and now he leaned out and pulled open a drawer in his bedside cabinet. He scrabbled inside, obviously seeking out his target without pulling everything else into view but succeeding only in perking my curiosity, and then turned back to me with a little pot in his hand a smile of success on his face.

"We might need this."

He showed it to as he unscrewed the top of the lube and placed it on the bed beside us.

There is only one purpose served by lube for two men in bed together as far as I was aware, and as realisation flashed through my mind I felt my heart jolt in my chest. Things were moving a bit fast for my liking and I was far from certain that I was ready for that step. I must have looked really anxious because Sam suddenly grinned at me.

"Don't worry; it's just there if we do happen to want it."

I must have looked as relieved as I felt at his assurance, even though I wasn't sure I believed him.

Because of the interruption we had ended up just lying side by side, but Sam rolled back to me intent on carrying on where he left off, and I wasn't going to argue, even though I was still eager to touch his cock some more. His lips fastened over mine once again, my arms went around his slender back and his long slim fingers cupped my balls again. All was right with the world for a second time.

With my eyes closed with pleasure kissing Sam was just like kissing a woman. He had soft, smooth skin, no bristles that I could detect, and the slim lithe frame of a girl. The only way I knew his gender was from the lack of breasts cushioned on my chest and the presence of his cock pressing against my hip, and I was getting used to that. If I'd stopped to think about it at that point I might have been worried for my sexuality, but what the hell, I was enjoying things. Being naked with Sam was beginning to feel quite normal and appropriate.

Sam's hand was exploring me further this time. He had left my balls to slide his palm down the inside of my thigh as far as he could reach, making me spread my legs a bit to accommodate him, then he crossed over and returned up the other leg, stroking my scrotum with his fingernails when he reached the top. He did this several times, each time gently encouraging me to open my legs and give him better contact with my balls. It felt wonderful especially as all the time I had his tongue in my mouth and his body gently rubbing itself against me. I didn't know where things were going, but it was getting highly erotic and very intense.

Otazel
Otazel
2,593 Followers