Mom hadn't been kidding about needing to talk more. We most certainly did have a serious family meeting the next day to define all of my expectations to keep on going out. The conditions were similar to the behavior contracts for most teens, except that my incentives were to dress up in lingerie and suck lots of cocks. I had to keep my grades up. I needed say when I was going out and get home by a decent hour, and not go anywhere with strangers or to all-adult parties. It was all pretty reasonable, I guess.
I couldn't let anyone hurt me, make me do anything really gross, or more generally force me to do something I didn't want to. I could always tell people to stop and leave immediately if they didn't. I couldn't use drugs besides drinking beer or take any money, and I had to use rubbers for fucking.
"That's fine. Why do men want to fuck boys instead of girls, anyway? We're not exactly made for it."
"It's an important decision for you. It can get messy, and it's much easier to catch something that way. Just tell us when you're ready." It was almost as if I was a teen girl. Mom and dad didn't let on that sissies like me really are made to get fucked, and that it felt so much better than jacking off I'd probably be hooked on it pretty quickly once I started. I didn't learn about that until later, for better or worse.
Mom wanted to talk with whomever it was who was hosting the parties. Not necessarily know who he was or where he lived, just talk and gage his intentions. I gave John our phone number when I saw him to suck his cock again on Tuesday. He called my folks that evening, and they went over the same do's and don'ts we had discussed earlier as a family. He was fine with all of it, of course. He was just a guy who enjoyed getting blowjobs from kids, not some sort of perverted molester.
I went on sucking cocks at the park after that and wondered when I might get invited to another party. Susan asked me about her lingerie after a few days when I didn't return it and I told her that I was wearing it to bed. I asked if I could keep it a little longer. She smirked and said not to worry about it until I could get some things of my own.
A few days later I overslept and came out to breakfast wearing her lingerie instead of switching back into my pajamas. Things began to change at home after that. Mom surprised me with several other cute sets of sleepwear and asked me to shave off what little body hair I had. She painted all my nails and did my makeup the next weekend, and then she also styled my hair. This was the mid-sixties, so it was long enough that I looked pretty girly once she'd finished with me.
It wasn't about sex for her, at least not at first. She just wanted me to be happy and comfortable, and to also see what it might have been like for her if I had been her daughter. But it was definitely all about sex for dad. He made me get down on my knees and suck him off immediately when he saw me fully en femme like that the first time. Mom just watched, pleased to see that her work was so effective.
Dad started "sneaking" into my bedroom every few nights for blowjobs. I use quotes because mom surely knew what was going on under her nose. Under my nose, actually. She really had no problems at all with her son being an incestuous sissy, and just saw it as more proof it was the right thing for me.
I was super excited when Susan invited me out again the following week. I'd been practicing regularly with the jelly to defeat my gag reflex and hoped I was ready to try some throating again. I told mom I had another party on Saturday night and endured yet another careful review of our contract.
The day came and mom had me shave and dress up in lingerie like I'd done the previous weekend. She'd bought me a bustier to shrink my waist, breast forms for simulated curves, and also some cute high-heeled sandals. There were a pair of elbow-length fingerless gloves, a short, lacey robe to wear over the bustier, and finally a pair of satin crotchless panties to give "my friend" (Susan) easier access to my clit. She did my nails, hair and makeup again, but much more provocatively this time. I was amazed at the transformation and was very grateful that she'd done so much just so I'd look good at the party.
"Thanks, mom. This is amazing."
"You'll be the best-looking girl in the room, Don." She sounded so sincere that I couldn't tell if she was kidding me or not.
"How will I get there looking like this?"
"Just wear some pants and throw on a jacket. No one will particularly notice the hair, makeup and heels after dark if you stick to side streets."
I left my glasses at home, since they didn't go with the outfit and I really wouldn't be needing them. At first I felt pretty vulnerable being out on the street that way, but I got over it. Walking in heels for a few blocks turned out to fairly easy. Almost as if I'd done it before, somehow.
Susan was ready for me when I arrived at her house. She wasn't expecting me to be done up yet and was pleasantly surprised at my appearance.
"Dawn! Your hair looks so nice, and I can't believe the makeup! You did all of this by yourself?"
"Um, thanks! My mom helped me get ready, actually."
"Your mom??"
"Yeah, she likes treating me like a girl now. Can't get enough of it. She's even buying me outfits and dressing me up, too." I opened up my jacket and showed Susan the bustier and fake breasts.
She smiled and giggled, more with me than at me. "You're such a sissy now you even get to have boobs. You said your parents were letting you go out again, but you look incredible! Does your dad know?"
"Yeah, they were both waiting up for me last time and we had a good heart-to-heart about the party."
"What did you tell them?"
"Pretty much the truth. They said they'd already suspected I was sucking cocks regularly on the way home from school. Mom even thinks I'm better off being a sissy instead of trying so hard to date girls."
"So, they're cool with it?"
"Well, they know what I'll be doing this evening and you can see how I'm dressed. I spent most of last weekend and today wearing lingerie just like this at home in front of them. And dad visits me in bed lots of nights now and has me suck his cock while I'm wearing your nightie!" I remembered that I hadn't returned it yet. "Ur, I can give it back now if you'd like."
"Go ahead and keep it. Sucking off daddy already? I'm impressed! Who knew both your parents would want you sissified like this! You're really very lucky, Dawn." Then she paused for a moment and looked slightly nervous. "But you didn't tell them I'm going with you or exactly where we're going?"
"Nothing specific. They didn't ask. I just got one more lecture about staying safe and being home before midnight."
"OK, let's get going. Shouldn't keep all those horny guys waiting!" I had nearly forgotten about the party for a minute while we were talking. "Bye, dad," she yelled back into her house.
"Bye. Have fun, but wrap it up by nine." Susan seemed embarrassed, and it was weird she had such an early curfew. She'd told me last time she'd left because of other plans, so I must be missing something.
We kept on talking on the way to the party. You couldn't exactly call it dating, but it was great I was finally getting to spend some time with a hot girl like Susan. Chatting also kept away all the butterflies I still got anticipating sucking cocks.
The group was about the same size as before and was very happy to see us. Everyone liked my hair, nails and makeup, and there were still more compliments once I stripped down to only lingerie. That certainly broke the ice, but at first we just sat down to talk and drink beer again. I got increasingly nervous about what was cumming next, but I remembered mom's advice about learning to manage it. And I was honestly a lot less anxious about giving blow jobs than I would have been asking a girl out.
It helped that I wasn't wearing glasses and couldn't always recognize everyone's faces. It somehow made me feel more anonymous, even if I was the one who couldn't identify them. I also had a couple of beers to help calm my nerves, but mostly just because had been fun giving head while fairly drunk at the first party and I wanted to do it again.
John spoke up. "Ready for playtime yet, Dawn?"
"Oh, yeah." He was making me ask for it, which was embarrassing and exciting at the same time.
"How's it going with the jelly?"
"Pretty good. I practice most nights when I have a chance." Could I be any clearer about wanting to get throated? Some guys snickered. I felt myself blushing but was still very eager to try.
I finally noticed that the furniture had already been rearranged with some extra space in front of and behind the couch. John handed me a few towels like it was my job to finish setting up, and I laid them out on the cushions and the carpet. Then I got in the same inverted position as before without being asked. Everyone else was just watching and waiting, Susan included.
John came over and knelt down next to me. There was a bulge in his pants and I thought he might be going first again, but he just took a small spray bottle out from his pocket. "This stuff will help with the gagging." The bottle was labeled "Cumfortably Numb Throat Spray," so I opened my mouth wide and let John paint the back of my throat. I could feel the numbness coming on in just a few seconds.
He moved away and one of the teens took his place. It was just "one of the teens" at that point, since I couldn't see him above the waist and hadn't thought to match up pairs of pants with faces earlier. I soon found myself sucking lots of anonymous cock this way at future parties. Guys would arrive late, enjoy a blow job with me kneeling or upside down, and then leave right away without taking any time to properly introduce themselves. So before very long I really couldn't tell you exactly which of the boys at school I'd sucked off, but I had to assume it was most of them eventually.
Classmate number one undid his pants and presented his cock to me. He was already fairly hard even before any stimulation, just like most of the teen boys I knew. His size was average and I wondered if they were having the smaller guys fuck my throat first before progressing to bigger cocks. That would make sense. He straddled my face like Ryan had and stuck his cock in my mouth without further preliminaries. All of my remaining butterflies quickly disappeared once the two of us started getting better acquainted this way.
I wasn't able to tickle his glans in this position since my tongue was on the opposite side of his cock. I wondered how much that would really matter, but he didn't seem to mind and his cockhead quickly popped on down into my throat. He penetrated another two inches or so until I'd swallowed everything he had without much trouble. Wow, I certainly had become cumfortably numb. This wasn't nearly as challenging as Ryan, let alone the jelly dildo. I realized I could actually do this and was pretty pleased with myself.
Someone standing behind the couch started caressing my inner thigh and fondling my clit. I knew that it had to be Susan and was immediately hard. "Look, Paul, she enjoys it. Use that little fuckface just like Ryan did." I got even hotter listening to her talk about me in third person that way, and imagined what everyone else must think of me while they watched the action.
Paul started stroking in and out, increasing his tempo once he saw I could take it. My throat was nearly empty on the backstroke and I could breathe through my nose if I timed it right. I just relaxed and let him use me as his penis hole while Susan kept me hot teasing my clit. All of my pleasure and excitement seemed to originate from wearing lingerie and servicing cock in front of a crowd, just like last time.
Paul was rigid and fully aroused in no time. His thrusts were urgent and his balls kept slapping up against my nose. "Fuck her hard, Paul. Go ahead and cum." There was no stopping him once he was ready. His body tensed and his cock pulsed, but I couldn't taste or feel his load as it shot down my throat. He relaxed once he had cum and pulled away from me after his cock started to soften.
Susan hadn't stopped teasing me, however. "That was pretty good, Dawn. You really do like it, don't you?" My clit was still hard, and I think she was a little surprised at just how willingly I'd submitted.
"I do, Susan, I do." I'd even surprised myself, honestly. I felt a real sense of accomplishment, like I'd just passed an initiation of sorts.
"Good girl—with a little more training your throat can be just as good a fuck hole as the cunt you wish it was." It wasn't a question. I looked around at all the other "trainers" in the room waiting for a chance to help out. This time hadn't been nearly as messy or exhausting as before, so I was ready to continue.
"Who's next?" asked Susan. Another kid came up and stuck his cock down my throat in a single thrust. He was already rock hard and came within seconds, which probably explained why he was in such a hurry. He must have overdone it stroking himself while watching me playing with Paul.
Susan stifled a giggle. "That was pretty fast. Don't know if we should count that one or not." It was always arousing hearing her belittle me, and I had no idea where a sweet teen girl like her had gotten to be so nasty. Don't worry, there's plenty more guys here waiting to take their turns."
I did three more boys after that. They all got off fairly quickly, but still took long enough to give my throat some proper practice. Susan laid her hand on my neck and told the room how she could feel their cocks moving inside me. I think I probably felt it more, but had no idea what it looked like.
All three of them had average cocks and I remained pretty comfortable until the numbing spray wore off. I was spasming and gagging as the last boy came but he couldn't care less. I started worrying I might really puke, but fortunately he pulled out pretty quickly once he finished. I coughed and sneezed up a mixture of cum and stomach juices while simultaneously gasping for breath, so it took me a little while before I could settle down.
"It feels awesome when your throat squeezes my cock like that. Just try to watch the gagging."
That didn't sound very sympathetic. I looked around at all the other guys stroking their cocks, and there wasn't much empathy in any of their faces, either. They were all still waiting to cum in my throat, even if it caused me what they viewed as a little mild discomfort. That's what sissies were made for, after all.
Mom had told me to set limits if I objected to something, but that wasn't the problem here. I was having fun and my clit was rock hard from Susan's teasing. I really liked having my throat used as a pussy but just needed a little more practice. "Can I have some more numbing spray?" I asked, working up my courage to continue. Susan said "That's a good sissy" and rewarded me with a nice little squeeze.
John came over and handed me a few tissues. "Let's take a break, Dawn. That was pretty good, but you don't need to master this in one night."
[To be continued. Send comments to laceyfemme@yahoo.com, and please consider making a donation to Nifty at https://donate.nifty.org/ .]