“I can’t believe we’re doing this,” I comment to my friend Jim as we walked into his house. We entered the front door of the large house, and I saw the Halloween decorations were all over the hallway. Jim’s mom usually got into Halloween, I guess that’s why she was cool with this.
“Why? Its not a big deal,” Jim commented casually. Maybe not for you, I thought, but didn’t say. I was about to live out one of my biggest fantasies, and I was just hoping I wouldn’t get too into it.
“Jim? Is that you?” Jim’s mom called from down the hallway.
“Yeah, Mom. And John’s here, too.”
“Oh good,” she leaned out of the kitchen, “Hey John. How are you?”
“Fine Mrs. B, thanks.”
“All ready for your big night?” she winked at me.
“Yeah, I think so,” I tried to sound nonchalant about it. Inside I was still reeling. I saw Jim’s mom was in a long black dress. I guessed she was going to do a witch or something along those lines.
“Your sister is upstairs, Jim. She’s all ready for you both. I want to finish the cupcakes for the party,” she headed back into the kitchen.
“C’mon let’s see what El has,” Jim started heading upstairs. I followed, trying to control my racing heart. It was amazing how a simple comment led me here. A few weeks ago as we waited for the bus to school, Jim was cracking every up as he usually did, then he busts out with, “Yeah, and I’m gonna be a hooker for Halloween.” Needless to say, as someone who had been experimenting with crossdressing this got my attention big time! Jim was one of those people that always did his own thing, and to hell with what anyone else thought. “Man, I’d never have the guts to go out like that,” was all I said. For some reason, it became Jim’s mission to convince me I could go out like that. Not that I really needed much convincing! His sister would even help us with the clothes and the make-up and stuff. Honestly, it was all a little too good to be true. I kept waiting for someone to pinch me and wake me up.
“El?” Jim called from the top step.
“Back here,” came Elsie’s reply. Elsie was Jim’s older sister. I didn’t really know her that well since she was several years older than Jim and I, plus she had already graduated. She was in the bathroom, working on her make-up. She was already in costume as a cheerleader. She smiled at me, “Hey John, so he roped you into this, too?”
“Yeah, he made it sound like it would be a real trip,” I said, still trying to play it cool.
“It should be, if nothing else the party should be as wild as ever,” she glanced in the mirror, then at us. “You guys go ahead and get changed. Jim, your stuff’s on your bed. John, there’s stuff for you in the spare bedroom. Yell if either of you need help.” She turned and looked at us both directly, “And don’t try to put the stockings on without help. You will rip them.”
My heart was hammering in my chest. I couldn’t believe this was about to happen. I almost turned and ran back down the steps, but then I calmed down and thought about it. Its Halloween, right? Lots of people get all crazy. Right? Why can’t I? Besides its just a local party. What was the worst that could happen?
I made my way down the hallway to the spare room. I was glad they’d put us separately. I wasn’t sure how much of my excitement I’d be able to contain. Normally when I dressed in my stash of stuff at home I’d be excited the whole time. I must have been too nervous this time, because I wasn’t even hard yet. Probably a good thing really, as I glanced at the pile of clothes, it looked like there wasn’t much material at all. I held each item up, going over it, feeling a slight shiver as I did. The top was a black bustier. It was PVC, too. I couldn’t believe the rush as I ran my hand over it.
Apparently, my whole theme was kinky, since the miniskirt was a red PVC number. It looked like it was going to be short, too. Maybe mid thigh if I was lucky, probably more like upper thigh if I was really lucky! The black fishnets were still in a little bag. I guess they got those new. I had given Jim some money for the costume a while ago, so I didn’t really know what it was going to be like. There was a black thong, though that wasn’t PVC. It was softer and silkier though. It wasn’t satin, but it felt nice whatever it was. Then there was a corset. A real deal corset, with laces and stays and everything. It was a bit worn, so I guessed it had been borrowed, or bought used, but I wasn’t too concerned. Though I did realized I didn’t have a clue how to put it on. There was also a belt like thing with some straps hanging down. It took me a moment to figure out it was a garter belt.
I was just about to yell for Elsie, when I heard Jim call, “Hey El, how do I get this lace-up thingy on?”
“Oh shit, I forgot about the corsets. Hang on Jim.” She knocked on the spare bedroom door. “Hey, you’re going to need help…”
I held up the corset, “With this? Yeah, I was just about to ask when Jim did.”
El gave me a quick smile. It also looked like there was a little gleam in her eye. It could have just been me though, I was about as high as you can get without chemical assistance.
“Here,” she said. She took the corset and held it up for me. I got a little timid about getting undressed, but El put it in perspective, “You’re going to be dressed like a hooker all night, you might as well get over being shy, right now.”
I pulled my t-shirt off and slid my arms into the shoulder straps. She helped me do the buckles on the front, then grabbed the laces in the back. “Ready?”
“Ready for wha… ooof!” I grunted as she pulled the laces tight. Not tight enough to cut off air or anything, but enough to make me aware of the corset. Also, enough to make me realize my sides were pushed in, and my chest was pushed up. I actually looked like I had some cleavage. “Okay, let me go help Jim. Yell when you’re ready for the stockings.”
I turned back to pile of clothes and slide the rest of my clothes off. Pulling up the panties was a familiar sensation, since I did that enough. I did a decent job of tucking my semi-hard cock into the panties, giving me that nice flat front. It took me a few moments to put on the garter belt and get it situated right. The skirt quickly followed that up. I relished the feel of the cool PVC sliding over my skin. I could really get used to this, I thought. I slid the bustier up over my head. The slick material felt really great, and it did very little to cover the décolletage that had been created by the corset. In fact the black really showed of the white skin of my chest. I considered briefly pulling my cock out and jerking off really fast, I knew I wouldn’t last long. But I also knew I wouldn’t have the guts to through with it then.
“El! I’m ready for the stockings.” I called down the hall.
“Okay,” the answer came from Jim’s room. I heard her say something to Jim, then come down to me. She entered the room, and looked a little surprised. “Hey, you look pretty good,” she smiled. I blushed, but didn’t say anything.
She showed me how to roll up the stocking like a little donut and slide my toes in first, then to roll the stocking up my leg. They felt so nice going on, though I wished they were the regular kind, and not fishnets. I guess you can’t have everything.
“Oh, and make sure you tuck the garter straps inside of your thong,” El added.
“Why?” I asked.
“Because, if the straps are outside your panties, you’ll have to undo them to take your panties off, if you need to go to the bathroom,” she stated simply.
“Oh,” I said, genuinely surprised. I’d never thought how complicated things could be like that. I tucked a few garter straps through the waistband. “Like this?”
“Yes, just like that. Then use the little hooks here to hold your stockings up.”
“Man, this is kind of complicated,” I commented.
“True,” El replied, “this is why so many women prefer pantyhose. Its much simpler.”
“So, why didn’t you get that?”
“Well, Jim said he wanted you guys to be as slutty as possible. And few things scream slut, like garter straps showing under a too short miniskirt. Besides fishnets scream slutty, too.” El smiled and laughed. “Okay, get the other stocking on and come down for your make-up.”
“El! This is stuck!” Jim yelled from the other room.
I finished rolling up the other stocking, relishing the feeling as always. The real rush was yet to come. I’d only really played around with make-up to this point, and had no idea what I was doing.
I headed into the hallway towards the bathroom and El came out at the same time. “Ready to be transformed?”
“As ready as I’ll ever be,” I claimed.
She sat me down in front of the bathroom mirror and began working away. I tried to watch as much as I could, maybe pick-up a few pointers, but it was hard with her working so much. I just know that Jim came in after a few minutes, bragging about how hot he looked. I had to admit, he didn’t look bad. He was a bit more muscular than me, so it was hard to really mistake him for a girl, but his outfit was way trashier than mine. They’d gone with a red tube top and black mini-skirt for Jim. He had stockings on, too. I could tell because the garters were sticking out of the hem. El was right, it did look pretty slutty. Jim was having a pretty good time of it.
I tried to sneak peeks when I could. I was amazed as the brushes and things ran over my face, how much less I looked like me each time I closed and opened my eyes. Finally, El said, “One last touch,” I felt her place something on my head.
A wig, I realized. Of course, my hair was way too short for anything else. I opened my eyes and stared in amazement. I almost gasped at how good I looked. Well, okay I looked like a tramp on the prowl, too. I mean it was pretty dramatic, but it was amazing. The jet black wig, the slutty make-up and the trampy outfit, I was pretty much set. I stood aside as El sat Jim down, and I tried to watch without paying too much attention to how she was putting the make-up on.
I realized I’d never be able to follow along and recreate, but I tried to get as much as I could. After a few minutes, she’d made Jim over into a trash queen, too. She placed a blonde wig on his head, and Jim said, “Now, we’ll get to see if blondes really do have more fun!”
El just shook her head. “Okay, I’ve got to get my make-up on, there are purses for both of you on Jim’s bed, and oh, shit! I forgot your shoes!” She giggled as she left the room, “You’re gonna love these!”
She came back a few moments later with some wicked looking stripper heels. They were open-toed pumps, with straps at the ankles, and 4 inch heels. Continuing the alternating trend, one pair was red, one was black. El handed me the red pair, Jim the black. “Get these on, and let mom know I’ll be ready to go in a few.”
Jim looked surprised, “Damn! I know you said you were getting heels, but aren’t these a bit... much?”
“You said you wanted to be slutty, that was the best I could find and not get too expensive. Now get!” She closed the bathroom door. She called from the other side of the door, “You might want put those on downstairs.”
I looked at Jim, “Why?”
He guessed, “Well, I don’t want to try the stairs in these stilts. Let’s go.”
We headed down and settled in the living room to get our footwear on. Jim was struggling with the buckles, I pretended like it was giving me a hard time, too.
“Oh, don’t you two look adorable,” Jim’s mom sarcastically said from the hallway. “Actually neither of you looks too bad. Need help with those?”
“Yeah,” Jim looked defeated.
“I guess so,” I shrugged.
She went over and helped Jim first. Once she got them buckled she told him, “The cupcakes are in the tray on the kitchen counter, grab them and take them out to the car.”
Jim got up and wobbled a bit when he stood. “Or you could practice a bit first, then take the cupcakes out.” Jim wobbled towards the kitchen trying to step carefully.
Jim’s mom came over to me and knelt down in front of me. She looked up at me with that twinkle in her eye again. “You know, I picked out the outfits for both of you. Do you like yours?”
I nodded, trying not to seem too eager. “Yes, its, well, I don’t know. Its different that’s for sure.”
She smiled as she finished buckling the shoe, “I got the corset, just for you. I thought it would be a nice touch you’d like,” she let her hand linger on my ankle for just a moment more than was appropriate.
She then stood, “Be a dear, and go help Jim with the cupcakes.”
I stood, and needed a moment to steady myself. Sure I’d worn heels before, but those were and inch or two. This was a whole new game. I practiced stepping carefully as I teetered off to the kitchen. El bounded downstairs, and we all headed out to the car.
I was beginning to get the hang of the heels, while Jim was still working on it a bit. Heading out the front door was a bit of a rush. I’d never been outside dressed before, but I was pretty sure this was something I’d want to do again.
The Halloween party in the neighborhood was something of an annual event, though it was held on the Friday or Saturday after Halloween, so it didn’t interfere with actual trick-or-treating. Every year a different family hosted, and it seemed to grow bigger each time. This year the Davis’ were hosting, and they had a big backyard that ensured there would be lots happening. We got there and the party was in full swing, the sun had just started to set, so everyone was starting to arrive.
I was a bit nervous heading up to the front door, but then I remembered everyone was in costume, and I knew from previous years that lots of women would be there dressed sexily, and each year a few guys came dressed as girls.
When we got there several people knew Jim’s mom and sister, and greeted them. They were shocked to hear the sexy hookers were me and Jim!
“Oh, you both have to enter the costume contest!” Mrs. Davis gushed. “You both look perfect!”
I was really surprised how much attention we were getting. Jim especially, since he would go out of his way to draw attention. This was his element, and he knew it, so he played it up like crazy.
I wasn’t too surprised at how many guys were checking us out. I was more surprised at how nasty some of the girls were looking at us. I guess it was just cattiness. I tried to not let that get to me, and enjoy the party.
We played games, someone started doing karaoke, and at some point in the evening, I got something to drink. After that the party really picked up, though I only remember some of it, since I had a bit too much to drink.
There were several incidents of note. One was the first time I went to the bathroom. I went in closed the door and went over to the toilet. I tried to work out the logistics of hiking up my skirt while pulling down my panties and was unable to come up with a good plan. So, I figured what the hell, and sat down, only to realize what El had been talking about earlier, my panties would only go down to the garter straps. So, I spent a few minutes unhooking those and rehooking them inside the panties. It did feel a bit strange to be sitting down to pee, but oh well. I checked out my make-up in the mirror, and decided to practice. I reapplied the lipstick and it didn’t look half bad. El had been pretty nice and left several things of make-up in the purse for me. I briefly wondered if Jim had them, too and figured he had. It seemed they were divvying things up well between us both.
I also had an interesting encounter with a guy from school, Don. I was coming down the hallway and Don was quite clearly looking me up and down, “Damn girl, you are smoking hot!”
I smiled shyly, and said, “Thank you. What’s your costume?”
“I’m a high school student,” he replied showing off his school jacket. Then he looked closer, “You’re a dude?”
“Yeah,” I replied. I was a bit nervous, not knowing how he’d react.
Don just shook his head and smiled a bit, “Well, you still look pretty damn good. You’re Jim’s friend, right? So, how much?”
“How much what?” I responded confused at his sudden question.
“Well, you’re a hooker, right? How much?” he laughed at his own wit.
“I don’t know, I hadn’t thought about it. I guess I’m not on duty yet,” I responded.
“Well, let me know if you feel like making a few bucks,” he winked and headed on down the hallway.
My head was reeling a bit both from the implication, and the suddenness of the encounter. I found myself a bit excited. Was it because he’d been interested? I’d always wondered if I was gay. I mean, after all, what straight guy would want to dress as a girl, right? But the idea was both exciting and frightening. Also, I hated to admit it, but for some reason, the idea of being paid for it, made me even more excited. What the hell was wrong with me?
I headed outside to get some air and clear my head. Though as I headed out, I discovered quite quickly that if I was going off the porch I’d have to do so barefoot. Apparently spike heels sink into the ground, another learning experience.
Jim came up to me as I came back in, “Come on!”
“What’s up?” I asked.
“The costume contest is getting ready to start,” he replied.
I hesitated, a bit uncertain. “I don’t think so,” I shook my head.
Jim tugged at my arm, “Come on! It’ll be fun, besides you’re already here, everyone’s seen you. What’s the difference?”
“The difference is I’m nervous enough. That will just freak me out more. You go, have fun,” I turned away.
Jim looked as though he was going to try more, but then shook his head and went over to the living room where the contest was being held.
There were several entrants, mostly typical Halloween fodder, witches and such. There was one girl who was a very sexy vampire that I thought looked good and put a lot of work into her costume. One guy was a knight and had head to toe armor. It looked pretty good, too. Not realistic or anything, but it didn’t look like cardboard either.
The vote was based on the crowd, which only pushed Jim more. He strutted and shook and had a good time with it. In the end, the guy who was the pinball game won overall, Jim got the prize for best guy’s costume, and the sexy vampire won for best girl’s. I was a bit disappointed I didn’t try, but I also knew I’d never show off like Jim, and the entrants who didn’t make a show of it didn’t get any response from the crowd.
El grabbed us after the contest, “Hey mom’s had a bit too much to drink and doesn’t look good. I’m gonna take her home, give me a call when you’re ready to come back.”
“Don’t worry about it,” Jim said. “Take care of mom, we’ll catch a ride with someone else.”
“You sure?” El asked.
“Yeah, its fine. Go ahead,” I replied.
“Okay, but if you can’t find a ride, give me a call,” El said and headed to the bathroom.
Jim went to go help.
So, I wandered off into the crowd again, not sure how I felt about having to bum a ride from someone. Maybe Jim wouldn’t be able to find a ride, and we’d have to call El anyway.
As if reading my mind, Jim came up a moment later, “El got mom loaded up, and don’t worry I found someone to give us a ride.”
“Okay, good,” I said again trying to sound nonchalant.
I managed to loosen up a bit after that, even started dancing around and having a little fun. I was really getting into it when Jim came up and tapped me on the shoulder. I leaned in close to hear him over the music, “Our ride is leaving, time to go.”
“Figures, I was just starting to get into this,” I replied.
“I know, I hated to disappoint you. You can always stay if you want, see if someone else will give you a ride.”
I considered it for a moment, what the hell, right?
“Yeah, I think that’s a good idea,” I replied.
“Really?” Jim seemed quite surprised, but then laughed, “Alright, you sure you’re going to be cool?”
“I’m good, thanks, and thank your sister for me,” I replied.
Jim headed off, and I returned to the dance floor to have some more fun. I had quite a good time, and even managed to get a few dance partners both male and female. I was going a little too strong after all the drinking though, and at some point got really tired.
I headed off to the side to sit down. It felt like it was going to be a minute, but it must have been longer, since I woke up and it was much later. The party was still going, but had quieted down some. At first, I was a bit disoriented, not remembering where I was or how I was dressed, but when I felt the corset and the thong hugging close to me, I remembered pretty damn fast!
I figured I’d better get heading home. My folks would expect me to be late, but it couldn’t be too late. I wandered around, but everyone I found was either drunk, staying or didn’t have a car. Finally I decided to just start walking. Brilliant, I know, but I was still pretty tipsy.
It was kind of nice to get out into the night air. And dressed as I was, I felt like a real streetwalker on the prowl. This feeling was only enhanced by a few cars slowing as they passed me.
The real shock was when one stopped! My heart leapt into my throat. What if they thought I was a real hooker! I mean, our neighborhood didn’t usually get that kind of stuff, but you never know what people might think. The passenger side window rolled down and I saw Don’s familiar face appear.
“Hey good looking, need a ride?” he grinned devilishly.
I looked into the car saw Chuck, Don’s best friend driving.
“I don’t want to be a bother,” I replied.
“No bother at all. Hop in,” Don opened the door and stepped out.
I hesitated briefly. Then hopped in. Don climbed in after me, and I slid down the bench seat a bit to make some room.
“Damn,” said Chuck. “You look fan-freaking-tastic.”
I blushed a bit, “Thanks.”
“I told you she looked awesome,” Don told Chuck as slid back in, moving over to be right next to me. I shifted nervously, and looked over at Don. He was smiling and looked me up and down again.
Chuck sped off, and Don put his hand on my knee. I looked up at him, “Listen Don…”
“Don’t worry, babe. I know you’re a pro, but I think you’ll really like this,” he interrupted.
“I… what? Listen maybe I should just…” I started.
“Get a little friendlier what a good idea,” Don finished and grabbed my hand putting it on his crotch. I could feel his rock hard cock through his jeans.
I pulled my hand back, but not as quickly as I should have. I hated to admit it, but the feeling was erotic.
“What’s the matter? Feeling a little shy? You don’t look shy. You don’t feel shy,” he whispered close to my ear. Then pressed his lips against my ear.
I gasped for a moment, then tensed, trying to push him away. He nibbled on my ear, and whispered, “Don’t fight, you know you want it. I saw you all night, you know. You really should be a girl.”
“Don, listen I can’t. I don’t want to, I need to get home,” I tried pushing him away again.
“Hey don’t be like that, I want to make you feel like the girl you should be,” he tried again.
“Don’t say that! I’m not a girl! It was just a stupid costume!” I blurted, realizing I was still slurring. I could also feel my panties starting to bulge. Damn it! I was getting excited now, too.
“You keep telling yourself that, you might believe it.” Don snorted, “So, are you going to do this, or what?”
“Do what? I thought you were offering me a ride?” I asked.
“We are, we just didn’t say where to. Besides you want to ride, you have to pay. And I know how girls like you pay,” Don laughed, emphasizing the words ‘like you’.
His words were exciting me again, but I tried to fight it. “No, I can’t.”
“Can’t, or won’t?” Don asked.
“Both,” I replied.
“Sounds like we got a little cocktease,” Chuck jumped in.
“Yeah, you know we don’t like being cockteased. I mean, I’d hate for word of this to get out,” Don smiled evilly.
“What… what do you mean?” I asked more than a little scared.
“Simple, I’d hate to have to tell everyone at school how a drunk little hooker got into the car and was all over me, even trying to pull my cock out. I bet that would make for a long school year. Of course, the gay guys might like you better,” Don detailed.
“You wouldn’t,” I stated.
“Try me, bitch. I like to get my way, and I’m going to get off on you, one way or another,” Don stated.
I looked him in the eyes, and I knew he wasn’t kidding around. I slumped down, defeated. “What do I have to do?” I asked quietly.
Don lifted my chin up, “Well, I did just want to make out with you, but now that you’ve pissed me off, I think you’re going to have to blow us. Both of us.”
My eyes popped out! “Wait! What? I can’t, I mean I’ve never…”
“You looking to piss me off more?” Don sounded angry now. He was a lot bigger than me. I was bit scared about where this could go.
“No,” I whimpered.
“Right then, prove it.” He leaned back in the seat, presenting his crotch to me.
I looked up at him and he cocked his head at me. I sighed, it was a good thing I was a little drunk, that would make this easier. I reached up for his belt and undid it, then undid his fly. He smiled down at me as I pulled the jeans down a bit and saw the huge bulge in his underwear.
“Oh, and you better be enthusiastic. You don’t have to like it, but you’d better sound like you love it. Lots of moaning and slurping, make it real slutty. Otherwise we’ll do it my way.”
I shuddered as a wave of excitement ran through me. I couldn’t believe I was getting excited over this! Of course, I was also scared out of my mind.
Chuck pulled off into a secluded area, and stopped the car. Don cleared his throat, he was getting impatient. So, I pulled down his underwear, and gasped slightly as his cock sprang free. I was amazed at how big it was, way bigger than my own. It had to be a good 9 inches, and pretty thick around.
“Impressed, huh? Most girls are,” Don said proudly.
I reached out touched it with first one finger, then began rubbing it with my whole hand. Running my fingers the length of the shaft, down to his balls and back up to the head. He must have been pretty excited, because his cockhead was purple and throbbing. I wrapped my hand around the shaft and began stroking gently at first, but getting used to the strange sensation, I found a steady rhythm. Don put his hand on my shoulder pushing me closer to his cock, “I wanted a blow job, not a hand job, slut.”
I shuddered again, a strange mix of fear and excitement, with the degrading names only adding to my mix of excitement and humiliation. I leaned in closer and stuck my tongue out licking the head. I traced the top with my tongue, which got a soft moan and a relaxing of the grip on my shoulder. I swirled my tongue around and then ran my tongue down the sensitive underside. This got more moans and so went all the way and began tonguing his balls. This went for a minute or so, until he put his hand under my chin pulling my face back up, he grabbed his cock and placed the head against my lips. I guessed he wanted me to suck now.
I started taking as much as I could, and got a little too enthusiastic, making myself gag and cough. As I recovered, I heard, “Yeah, gag on my big cock, you cocksucker.”
This time I found his humiliating comments getting my cock to stir. Since it was tucked away in my panties, it couldn’t get full staff, but was starting to make a very unladylike bulge. I caught my breath and went back to work, taking my time and sucking slowly and gently. This didn’t go over too well, I guess, because Don grabbed the back of my head and began shoving me deeper onto his cock, I tried to pull back but he was stronger, I could feel his cock hit the back of my throat. I put my hands on his thighs and tried to push back, but he had the leverage and was still getting all of his monster cock down my throat. I heard him say, “Grab her arms, Chuck.”
I felt first one hand then the other pulled behind me. Don then shoved again, pushing me all the way on his cock. I could feel his pubes tickle my nose and his cock stretched my throat. I must have been past the gag reflex, but I couldn’t breathe and was starting to struggle. That just turned him on more. “Yeah, fight it, you whore.” He pulled me up off his cock. “Now, I’m going to show you what I want.”
After a second to catch my breath, he shoved me back down onto his cock, spearing deep into my throat in one thrust. He then proceeded to fuck my mouth like it was a pussy. Shoving me down as he thrust up, he started grunting and calling me more and more nasty names. Finally he shoved me all the way down again and grunted and moaned really loud. I could feel his cock pulsing in my throat, shooting his load straight into me. He pulled back after a second or two and let the rest go in my mouth. He grunted and moaned some more, “Yeah, just a worthless little cum dump, that’s what you are.”
I sat trying to catch my breath for a moment, and Chuck let go of my arms. I slumped down, and was just about spit the strong thick cum from out of my mouth, “You better swallow that like a real slut would.” I hesitated for a moment, then resigned to my fate, I swallowed the creamy load. The taste wasn’t too bad, mostly just very strong. Don looked evilly at me, “Okay, Chuck’s turn.” I shuddered again.
As I turned the other way on the seat, I saw Chuck already had his pants undone and his cock out. His was smaller than Don’s but by no means small, probably a bit above average around 7 inches or so, but a bit thinner. I was just glad he wasn’t super hung, too. I moved over, determined to control the action this time. This time I started slowly again, licked and rubbing all over, but I moved to sucking much faster. As I started taking Chuck’s cock into my mouth and found a good rhythm, I felt Don’s hands running over the backs of my legs. Running his hands over the stockings was a incredible feeling, he spent a few minutes doing that. Getting me very excited and really horny. I must have been getting good at what I was doing orally because Chuck started moaning and making lots of noises. Don put one hand up my skirt and started rubbing my cock through my panties. This made me moan around Chuck’s cock, I was so pent up that I basically began dry humping his hand and really went to work on Chuck’s cock. While doing this Don used his other hand to hike up my skirt, and was rubbing and squeezing my ass.
I found that nice steady rhythm where I could suck deep and fast, getting him really excited. As his moans picked up, I could feel him tensing, Don did two things, first he started rubbing me faster getting me right to the edge, then as Chuck came and started shooting in my mouth, Don slid his finger into my ass as he finished stroking me off. I was lost for a moment in a haze of cum, my orgasm and pain / pleasure from being penetrated. I didn’t know which was up and came really hard, soaking my panties and Don’s hand in the process.
“Damn bitch! That was fucking hot,” Don commented.
I had to swallow the mouthful of cum that Chuck had just shot, “Thank you.” I smiled seductively.
Don smacked my ass, “I told you she’d make a hot little cock slut.”
I almost felt proud, if I hadn’t been so humiliated and embarrassed about what I’d done.
Don smiled wickedly again, as he held his jizz covered hand to me. “Now, lick my hand clean.”
I hesitated, not sure about it, but then figured what’s one more load? And licked Don’s hand clean.
“Alright Chuck, let’s get out little cunt here, home,” Don ran his over my ass and legs again.
Chuck pulled out and drove home, he flipped on the radio, since no one seemed to be talking. I was tired to the point of exhaustion, and ready to get undressed and take off my heels. My feet were pretty tired.
As we got closer to my house, Don turned down the radio, “Okay my little sissy slut, here’s how this is going to go. First, you don’t tell anyone about this, got it?”
Who was I going to tell? But I just nodded.
“Second, work on speaking in a feminine voice. Third, next Friday night we’re going to pick you up and you’re going out with us, wear this outfit under your regular clothes. Got it?”
I was shocked and stunned. “Wait! But I can’t go, I mean, my folks… and I don’t want to…”
Don looked mad, “Are you trying to piss me off? You want some more of what you got earlier? Then you’ll find a way, otherwise this will end up all over school.”
Don held up his cell phone and showed me a picture. It was me, my eyes closed and Chuck’s cock deep in my mouth. Well, shit. Now I was in for it. I sighed, and resigned myself to my fate, “Okay, Friday night then.”
Don smiled and patted my knee, “Don’t worry, you’ll have a good time, too. As long as you take care of us, we’ll take care of you.”
They dropped me off at my house and I climbed out, feeling like a dirty tramp in my clothes and I’m sure my make-up was a mess. Still I felt a little surge as I realized, I was probably going to get used like that next weekend. While I didn’t enjoy all of it, I certainly had some fun. I just hoped I could get used to it, I had a feeling I was going to be their personal cocksucker for some time.
I turned to trudge back home, feeling my cock stirring in my cold, wet panties. I could also feel my cum leaking out and running down my leg. For some reason, this completed me feeling like a little sissy slut.