I got a notification from a CD on NewTransNudes that they would be in Phoenix staying at a nice resort in a few weeks time and wanted to 'play'. Initially I though no way - I'd never done this before - though of course I'd thought about it many times. So I didn't reply at first but after a few days I went back and looked at his pictures - actually pretty horny stuff - cock - bigger than mine, nicely shaven, balls & pubes too. I started laying in bed at night thinking about playing with him and then started fantasizing about not just masturbating him but also sucking his cock.

I made the decision to contact him and we started discussing what we could/would do. He was all in for lingerie, masturbation, mild exhibitionism. Not so keen on fellatio, a solid no for him fellating me, but possibly open to me fellating him with a condom on. Not quite what I had hoped for but we agreed to meet at his resort's bar one evening he was in town.

The day came and I can say I was really not sure I'd be able to go though with it - but that evening I just decided to go for it. I set out with the large duffle bag of lingerie, toys & cameras I'd packed earlier. At the resort I parked far away from the bar and got changed in a quiet bathroom in the business center. I stripped and put on stockings and a suspender belt, open crotch panties, a cock & ball ring and 3 more ball rings. I then got redressed - my cock was already super hard with the anticipation!

I went to the pool bar and put my conspicuous duffle down on the bar (the pre-arranged signal). I ordered a beer and looked around - nobody appeared to be taking particular interest - after a few minutes a fellow started slowly making his way over to the bar - about my age... He came and sat next to me ordered a beer and struck up conversation. We covered some previously agreed topics exchanged names and chatted a bit meaninglessly about bland stuff as we finished our beers. He paid for the beers on his room tab and as he left he put a room key on the bar pointing to the number on the card fold. Then he left.

So I waited a few minuets - time to take another gulp - am I really ready? Yes - I got up and headed for his room. It was weird putting the key into a room door that was not mine - I wondered if he would be in lingerie already? The door opened and he welcomed me in looking just as he did at the bar. He said he wasn't sure I'd show up (me either). How to start was a bit awkward and I guess always is the first time - he'd done this before and suggested a game of looking at NBN pictures and guessing what the comments might include. It was a way of looking at sexy content with apparently a purpose other than just getting horny. My cock had been hard from the moment I left the bar - I didn't really need the slow start. Anyway the game was a strip tease based on incorrect guesses. Frankly I was trying to lose - I wanted my cock out on display and also wanted his cock out to see. But it took a while - which was at least a nice slow reveal for us both. He was in hold up stockings (at my request - since he usually favored pantyhose) his balls bound with stretchy cord that he had tied under his crotch up his back & around his waist. the net effect was that his balls were tight and pulled down & out emphasizing his shaft which looked mighty long. He gasped a little when he saw my cock & balls emerge ringed up tightly just like in my NBN pictures. He initially wanted us to refrain from touching but he gave that up when I started fondling him - balls first - then onto his shaft.

We moved over to the patio door and with some robes on popped outside to a small patio open to a shared walkway. Pretty risky if anyone came along. With our robes open he started wanking me for the first time. He had a cut cock while mine is uncut - he seemed quite fascinated working my foreskin, pulling it down tight then covering my cockhead up again. I guess it was all new to him and I too was enjoying the sensation - he also now seemed a lot more interested in my cock - promising. After I'd been wanking him off outside for a while we heard someone coming and retreated back inside. He led me over to the bed and encouraged me to lay down, he was taller than me and it seemed more comfortable for him this way. As I lay on the bed he knelt by my side and started wanking me slowly. I was now as hard as a rock and straining against his hand. Up & down, up & down, two hands on my cock, then one onto my balls, then rubbing my stockings and then my panties. On and on for a good long while slowly speeding up - then I felt the familiar feeling of sperm rising and started thrusting back at him. He was beating me hard with a big smile on his face until I finally erupted with a massive ejaculation all over his hands and arms, spurt after spurt, 3 days of cum saved up just for him. His smile faded a bit...

I was hoping he'd keep on handling my cummy cock as I softened but he was off in flash to the bathroom busy washing his hands. I though it a bit of an odd reaction. I was now rather hot so with the robe on I went out onto the patio again for air.

Almost immediately I started hardening again just at the thought of what we had done. In a minute or two he came back outside in some open crotch panties and seemed surprised that I was already wanking a fairly hard cock. However he seemed reluctant to touch my still spermy wet cock so I went in and cleaned & dried off a bit. When I came out again he'd taken his robe off and was sitting on a lounger slowly wanking himself. He looked really good - we were certainly taking risks here! I took off my robe too and knelt by him and took over wanking him slowly - he was encouraging me to go real slow as he said he had a bit of hair trigger when fully aroused. I was considering broaching the topic of me fellating him when he suggested we go to one of the resort spas for a bit. We'd discussed doing this in advance for a bit of exhibitionism depending on the situation and he'd arranged a room near one of the very secluded spas. We got out of our lingerie and restraints and into speedos as planned. Out at the spa there was nobody around and the spa light was out so it was ideal. We relaxed for a bit and got comfortable especially with the environment - then we removed our speedos and gently wanked each other under the water. I stood up and had him wank me out of the water - the exposure felt much better, then he stood up and I wanked him out of the water too. After a while I nuzzled my face up to his balls and started rubbing my face up onto his cock shaft. I looked up - he seemed to be absolutely loving it. I decided to make a move and started licking at his balls, all over. I looked up again - still loving it. I popped a ball in my mouth sucking on it gently, then I swapped to the other ball stretching it out from his sack a little, then I went in and took both his balls at the same time - a real mouthful. I was tugging on both gently looking up at him - I let one slide gently out, then the other. I moved closer and sucked on his shaft just above his balls - he was still with me. I did a bit of very gentle biting & sucking moving slowly up his shaft at the front. Nearing his glans I started to go back down all the way to his balls - then slowly back up again. This time he said "please dont stop - just keep going". So I kept moving up his shaft and started licking gently at the underside of his glans I stayed here for a while then he nodded his head at me - the meaning quite clear to me in the moment. I lifted my head and took his cockhead into my mouth, slowly taking him in & out - testing my abilities, I didn't want to start choking. I actually found it so much easier than sucking on a dildo or vibrator both of which I had of course practiced on. I realized I hadn't wanked my cock for ages yet still had a giant boner - turns out giving fellatio is a major turn on for me. The previous mentioned 'necessity' of a condom was aparently furthest from his mind.

Since it seemed clear to me that if I kept sucking he'd soon be cumming in my mouth I suggested we go back to his room - I wanted us both back in lingerie for that finale. In the spa everything felt good - but I really came out to suck off a crossdresser - hopefully on video - and right now we were both just buck naked having gay sex in a spa. It wasn't that I particularly minded that but I wanted the whole deal.

I did feel I could carry it through even though it would be my very first time - I was feeling good. Back in the room I lent him some of my lingerie to wear (stuff I find really hot on me - and on him too it turns out). Getting the stockings back on took a lot of drying off. Anyway time to get back to it - he wanted to be over by the open patio doors with the lights on. I said no, that level of exhibitionism & risk was just too much extra to be worried about while I was sucking my first ever cock to a cummy mouthful. I totally forgot to record the video with all the excitement - I'd brought a camera and tripod along - really kicked myself about this after, I'd missed my very first time.

Anyway I started more quickly this time - though in much the same manner. Balls first, work my way up his shaft then up onto his cockhead. I was more confident this time and took him quite deep to start with - in & out, in & out. I was going slow but insistently, occasionally coming off to give his balls a gentle suck (and to rest my mouth). I picked up the pace a little and soon after I could tell he was getting close. So - the moment of truth: I could stop and never know, or carry on and find out what a spurting cock feels like in your mouth, how his cum tastes and how a mouthful of cum feels. I carried on of course and started fondling his balls too - this sent him over the edge - his cock throbbed as he shot 3 small spurts into my mouth. I could taste his cum - nice, but there wasn't much volume. His cock was still throbbing but even sucking on it I was getting no more cum. I sucked gently on his balls again but he pulled away. I reached again for his cock but he didn't want that either. Again he disappeared quickly washed his hands and came back with a glass of water for me. By then I was standing wanking my hard cock. I was expecting a second wank at least, hoping even that he may have been inspired to kneel & fellate me too. But something was off again. He was now quickly taking the lingerie off. I was still wanking slowly wondering what on earth was going on - trying to be hopeful - then he looked at me again and said "I'm sorry but I don't think I can do this anymore". Basically he then rushed me into redressing, packing up and bundled me out with apologies. I suggested just going to the bar to talk about it - but that was a No too. What a bummer of an end to the evening.

Later in some follow-up messages he apologized further, said he always totally loses interest when he cums, feels ashamed and dirty and just wants to be alone. Said he was also sorry he came so little - but he had wanked out a big load in the afternoon just to be sure he didn't cum too prematurely with me.

All I can say is different people have very very different ideas of what to do.