Yes tell more

Yes tell more

And what happened?

Thanks for the comments and for everyone that takes the time to read my stories, you make a sissy very happy!

Anyway, so there I am, laying on the couch just in white panties and bra, stroking myself.
Jess, model like figure, average size tits, a couple of tattoos, lots of ear piercings, black hair (dyed this colour) in my lounge wearing a tight vest top and panties, watching me with her mouth half open in shock.
As you can imagine, I jumped up in complete surprise. I can't really remember whether I was trying to cover myself, trying to hide behind the couch or just saying ;'oh shit, shit shit'! but I know once the shock wore off I was just thinking ;'im so dead, she's going to tell Sarah!'.
Jess, after realising what her eyes had just been exposed too, pretty much said 'what the fuck' and turned to head back upstairs. In my panic, I stumbled across the room and quickly grabbed her arm and was begging her to stay here and talk to me. I say begging but it was pretty much desperation.
After a lot of 'begging' I managed to get her to sit on the couch with me. She had a lot of questions and I mean a lot! What are you wearing? Are you gay? Does Sarah know? Do you like wearing women's clothes?,,,, and many more.
The strange thing was the more I answered, the less nervous I felt. Even though I was worried about her telling Sarah, I was also getting excited. Also I noticed Jess's nipples had hardened so I was pretty sure it was having a similar effect on her.
So I told Jess I would do anything if she kept my secret from Sarah. Part of me thought, or maybe hoped, she would ask for me to get her off or even fuck her. She didn't ask that!..... probably because she could make out my small pathetic sissy cock in the lace panties. Instead she said 'I won't tell Sarah but I'm gona want you to do some things for me whenever I ask and just in case you don't do them, I'm taking some pictures of you that il keep. Iif you don't do what I want then I will either show Sarah or perhaps other people'.

So, that was a big moment for me. At the time I was in complete panic and pretty shocked by Jess however now looking back, it was the best thing that happened and really helped make me the sissy I am. Next time, I'll tell you what Jess had planned for me.

Yes tell us more

It was a week later that I heard from Jess. During that time I was pretty much panicking non-stop that Sarah would get a message from Jess giving away my secret. At the same time I had this strange exhilaration because my secret was in the hands of Jess.
Anyway, up pops a message on my phone. As soon as I see the name, Jess Watkins, my heart starts racing and my sissy cock starts tingling.
The text read 'Meet me tomorrow at 13:00 at Rosie's Mexican Cantina on University Drive'.

The rest of the day all I could think about was Jess' text. She had chosen my favourite restaurant but what did it mean? Surely we weren't going on a date! Jess didn't want me the other night so what was her game? I had to get time off work short notice to find out.

The next day I went to work as normal and so did Sarah. She was acting normal so there was no way Jess had told her anything. I couldn't concentrate at work, all I could think about was what Jess had planned.

So, at the agreed time I arrive at the restarant and find Jess already seated in a booth. She tells me to sit and we order some drinks. I ask Jess why we are having lunch together as it would be pretty hard explaining if Sarah saw us. She laughed and said 'we aren't having lunch silly, we are meeting someone'. I'm then thinking that she's invited Sarah and was going to tell her. To my surprise, suddenly this guy slides in the booth next to me. Jess smiles and says 'Michael meet Colin, Colin this is Michael who I've been telling you about'.
Colin, looks me over and says 'You were right Jess, he is cute!.
I'm somewhat shocked and lost for words. I look at Jess confused but also wondering who this guy is and what Jess has told him about me? The next thing Jess said blew my mind........
' Michael, this afternoon you're going to suck Colin's cock and I'm going to watch to make sure you do it and do it properly! You need to find out what a real cock is and not the pathetic thing I saw last week. If you don't do it then I'm going to show Sarah your cosplay pics'.

If you want to know more then you can wait for my next update. Alternatively, If you're in Huntsville then you might know Jess and can ask her or you might find me at Rosie's.

I'm not sure if there's much interest but I did promise to let you know what happened.

So off we go to Colin's apartment. On the way, all I can think about is that I'm going to give a guy a blowjob! I didn't even know how to give a blowjob? Yes of course I know the basics and what I've liked in the past, but that doesn't mean I know what I'm doing being on the other end. I was also thinking about Sarah. Was it worse to let Jess tell her my secret or to cheat on her with a guy?

Anyway, as with most things in my life, it didn't really go as I had quite imagined. We arrived and Colin led us to the bedroom where he immediately started to get undressed. Jess told me to do the same. It was at the point I was removing my jeans that I saw Colin naked for the first time. Even without him being erect, he had a fairly big cock. Certainly way bigger than my little sissy cock. I finished getting undressed, keeping my boxers in front of me to cover my embarrassment with both Colin and Jess watching me. Jess, of course, was having none of it and told me to drop them and stand by the bed where Colin was now laying. So I did what she said feeling both their eyes on my small cock.

So Jess then tells me that I have to do everything she says. At this point she starts removing her clothes until she is naked in front of us. I was shocked for words. What was she doing? I'd never seen Jess naked before. Her tits were a nice size but not quite as big as Sarah's and her pussy was totally smooth and neat. Sarah likes to keep a triangle of pubic hair so this view was unexpected.
Jess then tells me to stand and watch as she kneels between Colin's legs, takes hold of his now semi_hard cock, and starts licking and sucking it. Instead of looking into Colin's eyes, Jess is staring straight at me. I'm sure her eyes were smiling a wicked smile, her mouth wasn't because it had a cock in it which she was now sucking down to his balls.
I felt pretty humiliated standing naked, my little cock getting hard, watching Jess suck this guy off. It didn't go on for too long before she stopped and said 'now it's your turn Michael'.
By this time, I'd accepted the fact that it was going to happen. I was even a little excited. I got on the bed and knelt by Colin and took hold of his cock. I was surprised at how warm and hard it felt. It was pretty thick too. Jess told me to give it my best effort so I started by licking the shaft up and down. It still felt wet from when Jess had been sucking it. I eventually got the courage to put the tip in my mouth. I thought it would taste horrible but it didn't really taste of anything. I just gently sucked and tried to move my tongue around the head. I could hear Colin moan so perhaps I was doing OK. I tried to suck him deeper but I found it difficult and he was so big. I cupped his balls in my hand and kept sucking, moving my head up and down slowly so his cock slipped between my lips and some way into my mouth. I couldn't believe I was sucking my first cock and Jess was watching me in her birthday suit.

Jess seemed fairly impressed at my effort but she eventually took over and sucked Colin until he finished in her mouth. I thought my role was done until Jess grabbed me and kissed me, holding my head, forcing some of Colin's warm cum into my mouth.

So that was the day I sucked my first cock, tasted another guys cum and realised I wanted to be a sissy.

Next time you may get to really suck it till he cum’s in your mouth.

Great story, please keep it going!