This story took place a couple of weeks ago with a nervous cross dresser who wanted to meet with me, and they sounded ok and at least they seemed keen to meet up and I felt that they were genuine and that they would turn up.
I was a bit annoyed with them to start with as I did message them asking them to use the side door, mainly because we don't use out front door but once I let him in, I led him upstairs to my bedroom. I was already dressed up and I got him to strip off and reveal the red body stocking that he was wearing underneath his normal clothes. he was a similar age to me, but my only 5'10 tall and while red isn't my favourite colour for lingerie or stockings, the colour looked good his pale white skin. He also has some lovely red heels to match his outfit.
It was obvious he was a bit nervous, and he told me that I'd need to tell him what to do, so I took over and basically controlled the situation and led the way. I thought it was important just to give the guy a hug and let his hands stroke my stockings, my lingerie and my massive fake boobs. Neither of us were wearing knickers and I guided his nervous hand to touch and feel my cock, which is quite big and it was way bigger than his. I wouldn't exactly say that he had a micro penis, but it was tiny, poking out from his small ball sack.Before the meeting he told me "I am obviously nervous but excited. Been watching crossdresser porn for a couple of years and secretly wearing slutty lingerie - I'm in the closet so non convincing. I love your pics - your titties and your cock on turns me on!! Looking forward to seeing what happens"
I told him to wank my cock slowly and I asked him if he had ever sucked on a cock before? He told me that he hadn't, but had always wanted to and having seen my photos of mine, that's what he was here as he wanted to try sucking mine as his first one.
I told him that I was flattered by that and to mark the occasion, then I will take photos of him sucking on my cock for him to put on his profile. Naturally, he didn't want his face to be seen on the photos, so he asked if I had a hood or a mask that he could wear. I reached over to where I had laid out all of my things and I grabbed the first hood that came to hand. It was the one that I have which only has a hole for the mouth.
He put it on his head, and I motioned him to go down on his knees and be a good Sub and admire and caress my long stocking clad legs while gazing my cock. I told him what a naughty Sub that he was for coming to my house as a 'virgin' crossing dressing Sub wanting to suck on my cock while his hands ran up and down my legs.
Do you really want to suck on my big cock, do you, I asked of him, and he nodded and say yes Miss (not that I'd asked him to call me Miss, but that was ok). Well, you are lucky that forgave you for knocking on the wrong door I said before saying, go on them, take the tip of my cock in your mouth right now.
He did as he was told, and he gently kissed my swollen bell end and then gently wrapped his lips around the full tip of my cock. I was pleasantly surprised how good that he was given that he told me he'd never sucked a cock before. In fact, I was starting to think that he was too good at this to be an absolute beginner. But I gave him the benefit of the doubt and let him continue.
I praised him for his sucking and licking skills so far, but I told him that to have truly sucked on my cock, that he needs to take more of it into his mouth. he broke away from licking the tip of my cock and replied, "yes Miss" and slowly I slid my cock further into his mouth, but he couldn't take it all, but on a first go, I wasn't expecting him to. I didn't want to be so cruel to make him gag on it and potentially put him off cock sucking for life.
We continued like this for around 10 minutes or so and I told him to stop a couple of times as I didn't want to cum. I told him that I had another date in the evening, and I wanted to save my cum for them. So, at the point where I told him to stop, I thought it would be fun to see him on all fours on the bed and I told him to assume that position. I took some photos for him in that position for his profile and I also played with his arse which was nicely smooth. I assessed his hole with my finger, and it was really tight, and I told him that he if wants to be used as a Sub by me or by others, that he'd have to prepare his hole for fucking by having it stretched open. I took a photo of my cock resting on his arse crack.
I slapped his arse, and I also put my hand between his legs and played with his small cock and balls. I could sense that he had become excited after all of the cock sucking and having his arse played with a bit, so I told him to roll over on to his back and look up at me standing over him. I wanked my cock and I told him to do the same and within seconds his little cock was spraying cum over his leg and on to the duvet cover as he moaned and gave a sigh of relief as he laid on his back seemingly exhausted.
As a little treat, I moved down and gave his cock a little suck for the first time as I wanted to taste what his cum tasted like and it was nice enough, he winced a little bit as I don't think he expected that and I know myself, when I cum, my cock is very sensitive and I do enjoy having it sucked long after that initial orgasm. I also used my index finger to scoop up the cum that was on his inner thigh and I placed my finger in his mouth and made him lick the cum off my finger. I didn't care if he wanted to do this or not, as he was my Sub and to be fair, he licked the cum off my finger willingly. So, I scooped some more up that had landed on the duvet cover and made him lick that up as well.
After al that, I let him lay there for a couple of minutes and told him that he'd been a good Sub, but next time if he wanted to visit me, he'd have to be prepared to be fucked by my big cock. He said "yes Miss" again and I told him that he better get himself cleaned up and ready to leave, which he did.