I have known my buddy Jeff since high school. In fact, we may have even been friends before then, but my memory is fuzzy. For around fifteen years we were regularly in contact, often doing things together. He’d come visit my wife and I and we’d have dinner and watch movies together. We’d play XBOX games and go play pool at bars – just regular guy stuff.
However, Jeff and I hadn’t hooked up for a while though. Over the past couple of years we’ve only met up once or twice to shoot the breeze and complain about work pressure. I’m not entirely sure why this is. It could be any of a few possibilities or even a combination thereof – but let me explain further.
My buddy Jeff is gay. I am not, although there is more on that later. I am pretty darn heterosexual, and fell in love a long time ago with Charlene (my wife of a decade), who is a gorgeous, funny, intelligent and sexy woman. I could not ask for more! Aside from more sex, but isn’t this always the case?
Anyway, back to Jeff. I guess I knew from early on that he was gay – or at least bisexual. We’d visit each others homes, and it happened more than once that I stumbled across butch-muscle-bound guy on guy porn. Perhaps he knew that I found it – perhaps he wanted me to confront him, but that never happened. There may have been a few days or weeks of shock, but I got over it. He was my friend and would always remain as such.
I never really thought anything more of it. Like most guys, we never discussed our sexuality or inclinations in any way, shape or form. Perhaps the only ‘tell’ was that he did not leer at women, not that I do! I just try to be a gentleman about it. Use every bit of restraint to stick to the odd appreciative brief glance. Now and then I wondered how he dealt with his sexuality. Did he simply become comfortable enough to be “gay on the down low”? Or perhaps he was happy just masturbating with porn at home?
Jeff also started expanding his circle of friends a while ago. They were not people I could really get along with and as a result, he would attend a number of functions and events of which I attended a few, but could not really enjoy.
So while Jeff kept inviting me to “watch the game at the bar” or “come for a party at my new house” – I just kept declining them. At the same time, I asked him to come visit my wife and I for dinner and a movie or some such, but it just didn’t happen.
I do know that he and my wife had had a few conversations together that I let them keep in confidence. Being a guy, I’m not good at all that emotional feelings stuff. My wife also has a few gay friends that she got on with, but truth be told, they could’ve simply been discussing his family or other things. I don’t know that he shared any sexuality issues with her.
To summarize, I’m not really sure why we stopped meeting. It may have had to do with his circle of friends, or his sexuality or perhaps it related to being uncomfortable or not knowing how to respond when I flashed my knickers at him. And yes, you read that right. I said “when I flashed my knickers at him”.
You must understand that I grew up loved and well supported by my family, but did not have any female friends or schoolmates. I remained pretty innocent of anything sexual up until around 13 or 14 where I happened across some racy photos, magazines and some lingerie. Having had no exposure to this sort of stuff in the past, it related directly to my sexual awakening. I was seeing women in the occasional smuggled dirty magazine wearing clothing very similar to what I had in my hand. It had touched bare LADY skin! It had touched boobs and the thing between their legs! It was all utterly intoxicating and now having some years on me, I don’t hesitate a second in offering the clarity and wisdom of hindsight in describing my cock achieving a hardness akin to concrete. Over time I built up a little stash in a small brown school case, which I hid away. A pair of panties here, a magazine there.. a pair of lycra or spandex shorts that were too small and tight but felt deliciously naughty to wear.
It was during these school years and my awakening that I met and befriended another kid by the name of Anton, who lived a few houses up the road from me. For a long time, Anton and I just met to trade music and play computer games. The usual stuff. Except one day, Anton made a grab at my crotch. At first he did it in a playful way – just a bit of horseplay. But it did bring to light the fact that someone else might find me sexually desirable – and I was helpless not try and take advantage of it. Being a young and selfish teen, I did not understand or even both to try and understand sexuality in general. All I knew was that there was someone else who might want to touch my cock, and perhaps might let me touch his. So I started playing up to it. I would visit his house wearing a pair of shorts with nothing on underneath. In the confines of his bedroom with the door closed we would browse magazines, but his eyes would barely leave my crotch. On other days he would visit my house while my parents were out and I’d be “suprised” to see him, inviting him to my room while just wearing a towel after having gotten out the shower. Of course a legs crossed approach was taken while browsing magazines and of course he kept staring and finding some sort of reason to brush his hand across my cock to point something out in the magazine.
These encounters eventually stopped after a while, but not before attempting (with my heart pounding) a blow job. It was a failure, but that did not stop it from thrilling me. He told me something about his bum, and wanted to show me what he did to make himself cum, but I had no interest in that at all. I must just say that through all of this, never did I really consider gender or sexuality or any particular tendencies. Putting on a pair of panties and teasing another guy who desparately wanted to fondle my cock was just a bit of fun. Throughout all of this, it was still pictures of anonymous voluptuous women sticking their hands down their satin knickers that supported my throbbing cock.
Since then, I’ve come to realise that there are no clear borders when it comes to sexuality and attraction. Some people have very clear unwavering tendencies, and others have a grey area which moves about depending on their height of horniness. I believe it was this grey area that kept me wandering back to what I suppose is a crossdressing fetish. At one stage I broached the topic with my girlfriend of the time, but it was not received well and was subsequently dropped. To this day, my fixation has remained firmly in the closet and I have not talked about it in conversation with anyone aside from the odd internet stranger.
So in summary, I spent some of my teenage years with what I guess was a bit of a jackoff buddy (this ended after a year or so) and ended up marrying a fantastic woman a little later in life. Through all of this, Jeff and I kept hooking up and doing guy stuff together. As my wonderful marriage matured, like all marriages go – the daily bunny-sex started petering off. While this happened lingerie started forcing its way back into my conciousness. Over the recent years I started visiting womens clothing stores and nervously browsing through lacy thongs, selecting a couple to add to a small collection stashed in a hidey hole. When I had some alone time, I’d sometimes connect up a webcam and put on a bit of a cock-show. I’d put some stockings on, pull on a tiny pair of tight lacy panties and cover it with a tiny fluffy skirt. I’d aim the webcam at my crotch and connect to random sites. A ton of guys would connect and start messaging me. On the odd occasion, a woman or two would join the cam session and would egg it all on. I’d ask for her to flash me and in turn I’d flash our viewers – it would normally culminate in a spray of jizz covering silk and stock alike!
I’d also take some photos of myself and post them on various forums and groups, the latest of which has been flickr. I’d pose wearing various silk, satin and lace thongs and photograph myself while my member throbbed achingly, dripping precum about and soaking my small collection of garments. They were and are all completely anonymous, of course. I wouldn’t even give away clues based on backgrounds. Except this wasn’t enough. Around the same time I started wondering what adult stores were like – so I’d dress up from an underwear perspective and go and visit them. It was simply the thrill of entering a world that was previously unknown – an entire store dedicated to the wonderful state that is the orgasm. I would walk the aisles browsing various items, wondering which could possibly bring me the greatest pleasure. A vibrating buttplug perhaps? Maybe a cock ring? I settled on a purple vibrator with a bit of a head to it.
One of the stores had video booths. A small little room that one could watch a number of movie clips in – it took a dollar at a time. The booths were in another room and had small paper baskets in them, with tissues. I would rummage through the bins surreptitiously, looking for wet cum and damp tissues that I could bask in the smell of! On occasion, I’d wander about with my thong showing slightly over the top of my jeans and browse around.. I would enter video booths and pull the door mostly closed and “forget” to latch it properly. Nothing ever came of this, but caressing my cock through silk panties with my jeans around my ankles.. well, it was one of the biggest turn ons ever.
It was at times like these that I fantasized and thought that perhaps I wanted to be accosted by a stranger. I wanted to be forced to suck a strangers cock. I wanted to be covered in jizz. But the truth of the matter is when you take a step back and examine yourself and your motives in the harsh light of the day – none of these are things you really want. These strangers are real people. Often flawed people. Often unbathed, smelly, possibly even diseased. At no stage do you want to look in the mirror and point at the guy who greedily licked up the jizz of some random guy and in the process cheated on his wife.
So back to my friend Jeff. My friend Jeff is a known. He is gay and I know this, even though we haven’t discussed it and I don’t know whether he knows that I know. Self examination in the harsh light of day yet again reveals that should anything happen with Jeff, it would be cheating. But horny-brain justifies it. Horny brain says it would just be another type of fun that Jeff and I have together. It would not step over any particularly heavy moral boundaries since he is a trusted pal. So I took a few baby steps towards instigating something.
Jeff invited me over to his place. Perhaps to fetch something, or drop something off. Before leaving home, I sneaked a sexy thong out from my hidey hole. I kissed my wife goodbye and ventured off to Jeff. Along the way I stopped at a gas station and used the restroom – down slid my boxers which were already damp with anticipation. Up slid my thong. I pulled the elastic high so you could see the top if I bent down – much like hot chicks do when they wear low riding jeans. I got back in my car, already nursing a semi and proceeded to Jeffs place. Nothing happened. Whatever I may have flashed Jeff was studiously ignored even though my cock was straining at my pants at times. I kept waiting for some sort of “um, what are you wearing” at which point I might act all embarrased, confess a thing or two and possibly even explain it away as an adult store fetish but this was not to be.
And that is what I mean when I say that I flashed my knickers at Jeff. Perhaps on top of everything else that I’ve explained in terms of our relationship – perhaps none of that mattered, and he just didn’t want to be the guy that came onto a straight guy and jeopardised his marriage. Perhaps he was comfortable with coming onto me, but felt he would be betraying my wife Charlene. Perhaps perhaps perhaps.
But recently I got a call from him. He mentioned coming over for a drink and catch up. We chatted a while, trading war stories about work and how stressed and tired we constantly were. It was a good chat. Just before he hung up he mumbled something about checking my inbox. Puzzled, I looked. There was nothing there. Later that evening I had reason to check another email address. It related to my flickr profile. There was a message from someone, and an instruction! It read as follows “Visit a lingerie store. Tell the clerk that you you lost a bet and need something sexy to wear for halloween. Wear it!”…..
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