Sucking My First Tranny Cock

I'd been in chastity for 5 days, and my thoughts are not really focused on anything but sex (my lack of it) and sex (my desire for it).

Princess Melissa plans on keeping me in chastity for a long time. She says Sunday (4 days away), but I suspect she may be teasing me.

She told me I needed to suck cock and swallow some come - TODAY. So while I was at work I trolled CL for some options, and sent out some invites. I included some dirty pictures Princess had made me take of myself. By 4PM, still no takers.

But there's this massage therapist I know. I've been to her a few times. She is a beautiful T-girl, She has long black hair, great features and is trim and very passable. Well, we've talked openly, and I'm a good tipper. She thinks I'm sweet. She's given me a few hand jobs (wonderful ones that last 30 minutes) and one time asked to suck my cock (she did, and I could see in her eyes that she enjoyed it). I'd felt up her ass and she'd moan and sigh just like a real girl.

Well, she'd texted me to see if I needed a massage. I explained my current situation (chastity cage) and how Princess had told me I couldn't get out without sucking cock, drinking cum, and sending her pictures of it on my face. I stepped over the line and asked if she could help me with that.

I was nervous, because she'd told me that she really identifies as a woman, and is ashamed of her cock (never uses it for sex). She plans on eventually getting it removed. So for me to ask was pretty rude.

She initially said "no way - she could never do that because of her boyfriend..." I apologized.

But then I tried again. I clarified that the pictures would be of me, not us. I texted a few more times and then waited, sure I'd lost my favorite massage therapist, for nothing. ...I was very pleased 15 minutes later when I saw the text saying "I could do that"...So we set a time, and then I texted Princess Melissa. She was excited for me and urged me on.

Unfortunately I didn't have time to get dressed up, and my massage therapist doesn't like gurls. So I'd have to do this in my guy clothes, which is weird for me. I drove there, parked and texted. She told me to wait for a few minutes. That's when I saw she was sending her boyfriend away while she "worked a client".

She invited me in. She was wearing PJs and her boyfriend's boxers. She was still beautiful, but not decked out like usual. She explained that this was to avoid raising suspicions with her boyfriend. She also explained that she was really nervous, since she never uses that part of her. We hung out and talked for a while (20 minutes) to break the ice.

Then I asked her to come sit on the couch. She said no kissing (too intimate - this was just sex) and "don't touch the boobs" (recent implants, still sore - but very nice). I talked to her while I stroked her thighs and caressed her stomach (very trim). She really was nervous. I'd never seen her cock, and expected that it would be tiny because there was never a bulge or any sign of it, and because she was on hormones. She started stroking herself, saying she was worried she wouldn't be able to perform for me.

I pulled off her PJs, moved her hands and dove in. I did what I like, and pretty soon I could feel her little cock start to grow and harden in my mouth. I sucked hard, swirled the tip and bobbed up and down. Then she started to sigh...Finally she said "let's go to the bedroom".

I laid her on the bed, and resumed my work. By this time she'd grown to full size. Seriously a wonderful thick cock of about 7 inches. I was so pleased with myself as she sighed and said "I'm going to cum". She started to push my head away, but I kept going. I felt her cum in my mouth. It was warm, and different from my own. I could taste a little bit of weed in it. She blasted a few times and I let it partially fall from my mouth. I smeared it on my face and up and down her shaft. I wanted to take a picture for Princess Melissa, but she said I couldn't.

I stroked her shaft as it started to soften, cum on my face. Then she got up and cleaned herself off. I paid her, licked my lips and I left. I texted Princess Melissa, letting her know I'd done what she asked,

It was a long night in chastity again.