That evening abruptly answered all of my little questions around Susan, but it also triggered serious new ones about me. All of her little mysteries—mysterious departures, no boyfriend, way too many outfits, and of course being so relaxed and experienced at sex parties but never participating—suddenly made more sense if she was a hooker. I worried about her, but decided that all I could really do was keep on being her friend. And now I had a whole new collection of fantasies to keep me jerking off at night!
That was the easy part. The hard part was facing up to who I really was and what I was doing. I feared that being a sissy was honestly pretty second-rate compared with Susan fucking and sucking the way she could whenever she wanted. What I had to offer wasn't so bad, but it honestly wasn't the same.
Sucking cock at the park had been embarrassing at first, but I'd quickly felt very special and talented. I never lacked for men and teens seeking out my services and telling me I was good. Then I started dressing up and attending parties, and got even more approval and encouragement sucking cocks for whole groups of guys while wearing skimpy lingerie. I'd learned to use my throat as a pussy, and also got increasingly comfortable dressing up whenever and wherever I could. I really thought I had it down.
But I'd misunderstood what my skills, popularity, and new self-image really meant. I began thinking of being a sissy as close to being a girl, but all I was really doing was crossdressing and sucking cocks. Everyone called me "she" and thought I was girly, but only because I was such a slutty effeminate boy. I got so caught up in the masquerade I forgot that was the real reason men found me attractive.
Seeing Susan nude and watching her fuck made me understand the huge differences between being a girl and being girlish. Susan was a girl; I was girlish. Susan had nice tits, wide hips, and a pussy; I didn't. Susan got wet from foreplay and came when you fucked her, while I could massage a guy's cock using my throat muscles until I made him cum. Well...I guess the comparison wasn't entirely one sided.
I wasted way too much time worrying about this stuff. I eventually got a grip and went on with my life as normal—if you could call it normal—and just tried to separate out the emotional rewards I felt from sucking cock, looking like a girl, and feeling like a girl. I spent more time giving head and dressing up than usual, just to be sure. It was about a 60/40/0 split. The first two emotions were very powerful and reinforced each other, but I honestly didn't "feel like a girl" very much at all. I felt like a sissy cocksucker.
And that was just fine. I needed to accept who I was and move on. I was born this way, just like mom kept on telling me. I began to understand that not being a "real" girl was frankly better for me in some ways. It was one more way of being inadequate. Now I could feel inferior to girls for not having tits and pussy, just like I felt less than a real male on account of of my scrawny muscles and miniscule little clit.
And dressing up in lingerie and sucking cock wouldn't feel quite so humiliating and exciting as a girl, either. I would probably expect to have a boyfriend and for the sex to actually mean something. That part was nearly impossible to imagine. It would be next to normal, maybe even get boring after a while. Most guys told me that their girlfriends didn't even especially like giving blowjobs that much.
Enough about all my internal drama. The more important change from that evening was that Susan and I started spending much more time together. I would go over to her house after school most afternoons when I wasn't expected at the park, change into a sissy, and eat her pussy until she had cum two or three times and was well satisfied. She had this nice queen-sized bed she used for work, so it was a very comfortable and relaxing way to spend the time with her.
Eating her pussy was different from sucking cock (like I've already mentioned), and not only physically. It was always Susan's clit instead of a whole bunch of random, anonymous guys, and there was this actual bond between us because of our friendship and all the time she'd invested in training me. And it felt very special that a girl with Susan's looks and personality would have any use at all for someone like me. There was a definite emotional component to our time together. Not exactly like boyfriend and girlfriend, of course—something more like an owner with her beloved, well-trained pet.
I got pretty good at eating pussy with all that practice, and could eventually service Susan nearly to the point of exhaustion most afternoons. She said she was kicking herself for not thinking of it earlier, since it was the perfect loophole for her to have some fun without violating the rules her dad's bookies enforced about giving it away. It just hadn't occurred to her I'd be so good at it.
Before long I was as well trained to get excited and aroused from cunnilingus as I already got from sucking cock. I got to hear all about Susan's "dates" with her various customers in addition to the usual teasing. It reminded me of how she'd enticed me with the descriptions of sex with boyfriends when we'd first started talking nearly a year ago. She admitted that most of those "boyfriends" were actually some of her first customers. I found it much more exciting to hear her talk about fucking other guys than to fantasize about actually taking her that way myself.
Occasionally we'd finish early and there'd be a little extra time left over after she was satiated. She'd move down on the bed next to my clit and just enjoy casually stroking and licking me while we talked. It felt almost affectionate. I began to think that the girl might actually like me.
"You can't get enough of my stories, can you, Dawn? The way you like them makes me proud. I think you must like hearing about my adventures because you wish you were having them yourself."
"Well, maybe..." I didn't want to sound too excited, but my little girl was tattling on me again.
"You'd have real potential as a whore, cum to think of it. You're well over the hump of being shy and embarrassed about being used. You're docile and obedient, and care more about following orders and providing pleasure than anything else. You like playing with groups and being watched. And you're a teen boy who enjoys dressing up in lingerie to service adult men, which is always in demand. Your only problem would be handling the business side, since you're way too generous."
"There are boy prostitutes, then?" I was still really naïve in many ways in spite of everything.
"Definitely. Lots of men can't get enough of them, even if they're married and straight. Especially if they're married and `straight.' " I knew I'd seen plenty of wedding rings at the park and our parties.
It was tempting, but I still tried my best to resist. "My mom tells me I shouldn't take money from men, that they'll think they own me if I do."
"That's the whole point, silly! I know I've said it sucks to be told exactly what to do in bed, but you're different from me! That's just what you really need since you're so shy and submissive. You'll get stuck in this sissy cocksucker rut if you're not careful. Being a whore would push you to test your limits and try new things." She gave my clit an extra little lick for emphasis.
"Like what?"
"Like fucking, to start with. It's pathetic that you're still a virgin at seventeen."
"My mom..."
"Oh, screw your mom this once!" We both giggled at the idea. "Metaphorically, I mean...she doesn't always know what's best for you. Take it from me, you'll enjoy it. Men fuck my ass all the time now to dominate me and for the change of pace. It hurt at first, but you'll start liking it if you just relax, take it slow, and use enough lube. You learned to throat fuck, didn't you? And it's even better if you're a boy."
"Why? It's not like I have another clit back there." Like I said, I was pretty naïve.
"Um, you really do deep inside. They say it feels amazing for sissies when a cock or toy rubs up against it. It can even make you cum, shoot juice out your clit and everything."
"Really???"
"Do you think I could possibly make that one up just to fool you?" My mom had some explaining to do if I could figure out a way to raise the subject innocently.
"I'm just saying it's a big world, Dawn. There's lots of places you can go, and whoring could be your passport. Think about it."
"People think it's slavery, but it's really just another transaction." My mom had used that word. "Guys don't abuse me any more than they'd want to hurt someone washing their car." And it probably pays better. "They just want to have fun with me. It can get pretty hot sometimes."
"There's this one married couple I really like, for example. They're somewhere in their early forties and thirties and have kept in good shape. They have a kid, so we can't get together as much as they'd like to. As much as I'd like to, honestly."
"I ate the wife's pussy last weekend while her husband took turns fucking me from behind in both holes. I made her cum, and then we sixty-nined with me on top. The guy had three holes to enjoy that way until he finally came in my cunt. Then the she cleaned up her husband's cum and got me off before much longer. We all wanted to do more, but their kid was coming back soon and I had to get going."
"Doesn't that sound like fun, Dawn? That could be you instead of me. The three of you could have great times together."
My clit was rock hard. She took me in her mouth, and I came before you could say gay teen prostitute.
All that teenage bliss ended suddenly one afternoon two weeks after school finished. "Dawn, I need to tell you something," Susan said after making me cum again at the end of our playtime. "What, Susan?" She looked very serious.
"This is our last time together. I'm leaving tomorrow to move cross-country with my folks. They say it's the only way to be certain of escaping the bookies. There's no other choice."
We hugged and kissed, and she fed me back my cum one final time. She held me like she really meant it and we even cried a little. Then we had to get dressed and it was time to go.
"Take these." Susan handed me another bag of clothes and lingerie sets for my huge collection of outfits I'd never returned. "I know your clit likes them." She smiled, unable to resist one more tease.
"Thanks, Susan. I'll always remember you. Things will work out." I didn't feel that way.
"Goodbye, Dawn."
"Goodbye."
[To be continued. Send comments to laceyfemme@yahoo.com, and please consider making a donation to Nifty at https://donate.nifty.org/ .]