Daniel & Alex's Very First Time

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Inviting Daniel into my life.
3.3k words
4.36
27.6k
2

Part 2 of the 2 part series

Updated 09/22/2022
Created 01/05/2011
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alexcarr
alexcarr
331 Followers

A true story by Alex Carr.

Thinking about it I did absolutely the right thing inviting Daniel into my life.

I was bi-sexual curious having been married for thirty years, out sexual appetite having some way diminished although we still love each other.

But looking back to my service days in the RAF I have been close to going the full way with another guy called Bernard. I remember with affection now getting into his bed one night, we'd both had too much to drink but despite that I remember so clearly doing something with him I'd always wanted to do when sober, but had never had the courage to.

N

Snuggled up behind him I enjoyed the feel of him and remember distinctly how he ejaculated into my hand after just a few squeezes and jerking movements. After that I just returned to my bed, masturbated and fell asleep, the next morning nothing was said and it was as if nothing had happened.

However my curiosity was abound, I wasn't married at that time so didn't know which way I was going, after sharing some conversation with him about girls and the like, as guys together do, I suggested we should go to the bathroom and he agreed.

I don't remember much about that because it was a complete failure, despite frantic mutual masturbation he was unable to enter me so that was that. W never spoke much again.

But later and married I knew I still had a leaning towards my own sex and when my wife worked different shifts to me in a local hospital and I had some time alone I took to dressing up in my wife's clothes, especially the revealing underwear I'd enjoyed her wearing so many times.

It had a positive effect on me, I felt a certain hunger for the want of the right word, in my back passage - I shall call it Henry because most other references seem so crude to something I thought was so very special and wonderful.

Imagining myself as a girl I would practice with all manner of tools and whatever, as long as they had a nice smooth bulbous handle that substituted for a penis. This was before I got into anal vibrators and things which I purchased in a local 'private' shop.

Looking back now it seems crazy the things I use to do but it was jolly nice and very sensual - even though it seems all very funny now thinking about how I used to lay stark naked on the floor with a long mirror well placed to watch Henry being entered with a screwdriver handle, carrot (shaped to look like a penis) a broom handle, a cucumber (of course) - after slowly and provocatively raising my skirt to reveal black stockings and suspender belt and slowly but effectively raising my ardour with the teasing of finger tips aro0und the genitals until I found myself craving, after due lubrication, for the feel of something u there inside me.

I experimented thrusting and moving it in different directions, I discovered just walking about and carrying on the daily duties at home, pretending I was a gorgeous female, was very aspiring, once I got the knack of stopping the vibrator popping out of me with well applied surgical tape. I managed to reach a climax several times this was although massaging my cock did not always work in perfect unison with the feeling inside me.

Often wondered how my wife would react if she had known about my bi-sexual tendencies but she never has so what she the heart doesn't bleed for what she doesn't know about, even afterwards when I regularly enjoyed Daniels fuck and everything else we did together...

Getting bored with the do it yourself thing I wanted much more, knowing I was plainly bi-sexual I craved to be with a real guy in the flesh, but of course he had to be the right guy, someone I could really like and more - because for me emotions always play a big part.

But that was more difficult than one can imagine. I went onto the Utopia Gay chat room on the net and tried to arrange a date with several. But it was always the same thing, all they seemed to want is a cheap thrill exchanging revealing pictures and ;doing it' on Skype to which I could never get true satisfaction.

Even a couple of guys who did look serious did not turn up at a planned meeting place which I found very frustrating after getting myself all hyped up for a real carnal adventure, taking into consideration all those things we had chatted about online and all the things we'd like to do with each other.

It was all too much and I was near to the end of my tether, almost degrading myself to doing the toilet basher bit to relieve my ardent sexual need - but the thought of that revolted me plus the chance of getting caught and all that would mean.

But all was not lost. I discovered Daniel who lived just five miles away so there was no problem with travel. He was divorced and like me bi sexual curious, he lived with his ageing mother though so it was awkward for us to meet and do our thing in his place.

Anyway I said at least let us meet and see if we are compatible with each other in real life because we seemed to have been getting on s well together online and what I liked about Daniel, he wasn't pressing and I had a feeling he was, like me, genuine.

There was a problem also as far as I was concerned, should I invite him to my home when my wife was working or what?

We decided to meet in Morrison's car park with an identification tag and he giving me the registration number of his car. Great, this guy really did seem to mean business so I made sure I was prompt at noon to meet him.

My heart was beating twice the normal with the thrill of the idea, and the thought always of just being intimate withy a real live member of the same sex. By then I had fantasised so much of just how it would be like, how would it feel and everything, and even as I looked for his car number the swell of things to come was positively there bulging in my pants, the excitement was excruciating and just hoped to God this guy would turn up.

I needn't have worried, I saw this guy waving behind his windscreen and somehow from that point I just felt so comfortable, there was something about his welcoming smile, his charisma as he opened the passenger door and invited me to join him.

We exchanged greetings and then he asked was there somewhere we could be more private. Of course at that time I didn't want to take the plunge and invite him to my place before we got more acquainted and I knew he could be prudent so |I suggested a disused car park about a mile away and as we drove there I began to feel like I had known this guy for ages because he seemed so right, and we both had so much in common.

When we got there I suggested parking near the surrounding trees which would give us some cover although he seemed a little nervous and I knew then he didn't want to take any chances and wanted t be just as prudent as me.

He explained his problems in not being able to invite me to his place - I felt the need for him big time and said I would arrange something for the weekend when my wife was working, on Sunday morning in fact.

But I felt there was a need for me to start something and it seemed easy for me just to move my hand over his crotch and get the feel of him as we talked about all the things we had done, surprisingly similar in so many ways even to masturbating before a mirror and imagining being with another guy, although he told me he had not ever and that all this was a new experience for him, but he certainly showed he he enjoyed what I was doing when I started to squeeze him through his jeans, when he parted his thighs and let me unzip him.

I soon discovered he had a lovely seized cock on him and found myself concentrating on the moment in hand, it was so much nicer to be feeling another rather than one's own because you could not anticipate the next movement or whatever. It felt so lovely and appealing, especially with Daniel

His eyes focussed on mine, enjoying that certain intimacy between two guys. I sniffed the scent of him, not dissimilar to my own when I sniff the palm of my hand after masturbation - thinking that was a good omen, that were chemically similar, I had read somewhere that was half the battle when making it with a new partner.

We'd ascertained our leanings, in as much as he was quite happy to be the giver if I was being the taker, the truth being, and that is why my heterosexual marriage has failed in a physical sense, is that I cannot maintain a permanent erection and (I think) have become so much more hormonal female, that I am not longer turned on that way.

As I stroked Daniel he swept back his head and closed his eyes and I just could not help myself, this would be the very first time I had sucked cock and do you know what?, it just seemed sp perfectly natural and loving even with Daniel.. I leant my head down to him, to take in some more of his scent, especially as I eased the foreskin back to reveal the beautiful head, Daniel murmured words of comfort saying I was so good and how he loved the way I just helped myself.

I certainly intended to as first I wanted to experience the taste of him, I licked it first, gradually to take in the flavour, I felt his cock staring to throb in my hand as it grew and grew, it must have been a good seven inches or more, and I was thinking was certainly bigger than anything I had put up there, but it would be alright I felt sure - and anyway I would prepare myself with something just a little bit bigger for the special occasion and anticipation of our very first fuck together.

I opened my mouth wider and took as much of it into it as I could, it was simply lovely to feel and suck nice and slowly hearing Daniels appreciation.

I was enjoying it so much and suddenly began to realise just what I had been really missing all those years, but was the time to make up for all that now and if Daniel was game so was I.

But our pleasure was spoilt by a police car which came into the car park causing Daniel to push my head away with a slurp, because my mouth was well and truly attached to his cock, and like a flash, ticked his dwindling cock into his jeans and zipped himself up pronto.

And that was so nice too. But of course I realised his caution and we accepted that the only thing was for us to meet at my place on Sunday, and I was happy to agree with that now I felt comfortable about his prudent ways.

So we departed on the promise that we would complete what we started on Sunday. Roll on!

We kept in touch with the mobile phone too. He came for me over the phone which was nice and another first, it came about because of our talking abgo0ut how nice it was in the car park and how he loved what I did to his cock.

I could still taste it in my mouth, now I wanted to feel that beautiful length inside me, I was aching for it and vowed on Sunday morning before Daniel arrived, and remembering how Bernard could not get it up me, to insert a bigger screwdriver handle into Henry and let it keep there inside me enough for it to str4etch wide enough for dear Daniel.

I told him what I would do but he assured me not to worry, that he would get it inside me even if it took and hour, that he had heard first time was never easy and we both needed to work on it, and anyway that was 0part of the fun.

That how dear Daniel was, so considerate and understanding, I felt my whole being wanting him and when at last there he was, standing at my front door with a bulge full of ready (as I teased) .

I led him into the bathroom, asked if he would like to get undressed and closed the door after him from the outside.

But I was so eager I just could not help myself and just had to take a peek to watch him undress.

HE saw me and chuckled, holding his beauty in his right hand and saying " well here it is then" as if to invite me to enjoy, I was certainly intending to and soon I was standing there - after Daniel helped me undress, I saw that he sniffed my briefs which was so nice and I felt flattered, I picked his up from where he had places them an the bathroom stool along with his other gear and let him see me sniffing his.

Then, still sniffing, we started to enjoy touching and feeling each other, at the same time - that magic again in looking into each others eyes, we started to gently masturbate and it was heavenly, feeling its pliancy and remembering its heavenly pungent and earthy taste.

Soon he put his hands on my shoulders, prompting me to go down on my knees and I immediately knew why, he leant backwards to give his cock a good showing and, with my hands at the back of me I found his erection with my mouth and started to lick its length, right down and further down to his firm balls so full and ready, it was heavenly, it really was, I must admit I made a feast of it but Daniel was more than happy with that telling me he was going to fuck me like I have never been before, which I chuckled wouldn't be hard because I had never been fucked before by a man and up the ass.

He responded, in between his moans of pleasure, saying he would soon put that to rights as I had the most delightful fuckable ass for a fifty year old.

It was true I was fifteen years his senior so for me it was lovely to have young cock all to myself, something I knew then I would become very attached to in more ways than one

"Don't be too much of a pig!" he said pushing my head back, away from his throbbing cock.

"Only because we need to save him - I need your fuck so much, now let me have a sniff, my turn Huh, Alex?" he said.

And of course I was game, just bend for me, bend it nicely over the edge the bath.!"

He places the bath towel doubled over the edge to make it more comfortable promoted me to lean over as much as I could.

It was so lovely and I shall never ever forget just how thrilling and wonderful that first time was, it felt he was absolutely devouring my all when was spread-eagled across the bath edge and I shall never forget those first heavenly feelings as his tongue and mouth worked in unison into my ass, his hands nudging and squeezing my cheeks, spreading and licking between, OMG!how wonderful was that!

I just wanted to be all ass for him, I wanted to be all that was quality and perfect, I swayed it and he said he adored that, not to stop and then he slapped it, just lightly but enough to make me feel so good and belonging.

Then he raised his head up away from the crease of my ass and took a good long breather saying that was the most wonderful thing he had ever experienced, of course it was his first time too so we were both an a par. And that meant so much.

"Eat me once more before I fuck you, Alex? He asked and I wasn't slow to take up the offer. I felt Henry was well and truly read for him, well lubricated beforehand and well sucked and prepared, now I was preparing Daniel for the final furlong, that wonderful first thrust into my aching ass!.

I closed my eyes and he pulled away from me saying he was ready and prompted me over the bath edge again, I remember a sort of silence as I waited for it. And when I got the first touch it was a little higher than it should be and I was thinking he had not found the right place. But then I realised it was just his way, rubbing his erection between my crotch until very gradually it found its place, Daniel started to work it inside me, gently and slowly, it was so good, such a wonderful warm feeling too, then harder stiffer it started to slip inside, a little at a time, I was helping him work it up into me by swaying my hips too and fro, gradually it moved deeper into me and I could feel a sort of light aching which soon went again once I had been stretched further inside, but all that I could do with the substitutes like the vibrator in moving my rectal muscles and squeezing - I could not, because his bulk was so absolutely tight inside me.

I yelled and he asked me if it was alright, no way was I going to complain even though it did hurt for a while as he piled it into me, I felt like I was being split but I gritted my teeth and started to enjoy the fuck as he worked it fully up inside.

"I don't have a condom is that okay, Alex?" Daniel said pausing a while, me feeling his deep strong throb inside me. The last thing I wanted then, deep in the thrill of his fuck, was for him to take it out and put on a condom, I felt I wanted to feel flesh against flesh you see and not hindered by a sheath of rubber.

I said it was fine and he slapped my ass profoundly and got on with the fucking whi9ch I enjoyed very much because a sort of numbness had set in to dispel the first fuck pangs and so it felt alright.

I felt his weight pushing and pushing, my head touching the bottom of the bath, he had me at his mercy and I realised I enjoyed that, It was all part of the belonging syndrome.

We both indulged for a good ten minutes, Daniel occasionally stopping to take a breather and it was heavenly to feel its constant throb inside.

When he breathed was it alright to cum inside me I knew his fuck would soon be done and my bi-sexual curiously satisfied.

I said I wanted that and do you know? He gave me the most wonderfully stimulating firm and rapid masturbation aver as he really went to town and fucked me hard and roughly, soon I was there with him, I felt my cum squirt into his hand and the feeling of that and being fucked at the same time was absolutely fantastic.

He grunted, wiped my cream over his face as we both ended up sprawled and breathless on the bathroom floor.

And that was just the first glorious time with Daniel with lots more to come...

alexcarr
alexcarr
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Riki1942Riki1942over 1 year ago

Like the anonymous comment above, I am also a crossdresser, but totally gay. Although I don't want to be a real woman, there have been few times that I have had sex and not fully cross-dressed and wearing makeup.

There have only been a few guys that I have gotten to know well enough and had an ongoing relationship with that fucked me bareback, but I can certainly empathize the need to not use condoms.

It's not so much that the feeling is so different with a condom than bareback, at least until he cums, but more the psychological aspect of it. It's infinitely more exciting and arousing to know it's the real thing; his naked cock inside me and that I am actually going to have his sperm inside me!

AnonymousAnonymousabout 13 years ago
Daniel & Alex Very First Time

I am a male to female bisexual crossdresser and enjoyed the story very much.

Sincerely,

Josie of Augusta, Georgia USA

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