Chapter 3
My phone rang and I saw it was Brad from the Costumes 'n' More shop where I’d been working recently, and playing, if we're being honest. I answered excitedly hoping he was ready for me to come down again, so to speak.
“Hey, uh… Tom, it's Brad,” he said somewhat hesitantly. I wondered why he was hesitant, I debated answering in my femme voice since I’d been practicing it like Anna had taught me, but I didn’t want to confuse him, not at first anyway.
“Yeah, I know,” I answered brightly, “What’s up?”
“Oh good, yeah, so listen, there’s a couple things. First, are you still good for your next costume showing tonight,” he stated rather than truly asking, sounding a little more sure of himself now.
“That sounds wonderful, hun! Do I get to know what it is?” I asked in my best femme voice, I hoped it sounded good.
“I… whoa, that sounds wild. Have you been practicing?” he asked, sounding a bit thrown off again.
“Yes, I have!” I replied keeping the voice, figuring this was the best way to practice. “Is it okay?”
“I… yeah, it sounds good,” he replied. “Uhm, kinda sexy actually.”
“Oh really?” I practically purred back. “Hopefully I can show you more tonight.”
“I’d really like that,” Brad said back, I could practically hear him grinning.
“So, was there something else?” I asked softly, not really wanting to disturb the moment.
“Oh, uh yeah, the boss, my Manager wants to meet you. I think he wants to talk about working at more locations, and maybe that calendar thing I mentioned,” he said quickly.
“So, you told him I’m not available… or something, right?” I said moving back to my regular voice.
“Well, I just told him I’d let you know. I didn’t want to speak for you. What you do with that is up to you,” he explained. He gave me the number to the office so I could schedule an appointment.
“And did you tell him who I really am?” I asked uncertainly.
“We didn’t really get into that,” he answered quickly.
“So, what should I wear?” I asked.
“I… I don’t know, I hadn’t really thought about that,” he said.
“Welcome to my world,” I replied. “Okay, was that everything?”
“No, Anna wants to talk with you when you come in, too.”
“Okay, any chance you’re going to tell me the costume, or do I have to wait?”
“I like it to be a surprise,” he laughed back.
“Fine… hopefully there’ll be lots of surprises,” I added mysteriously.
“Yeah,” he added distractedly. “So, I’ll see you later?”
“Ab-so-lutely!”
I hung up and looked forward to heading in. I had some time to kill, but wanted to make sure I got a shower and did all my preparations. I decided, against my better judgment, to call the big boss. Thankfully he wasn’t in, but they were able to schedule me an appointment to come in the following week, so that would give me some time to think of how I was going to approach that.
I stepped into a nice warm shower and let my concerns wash away with the water. I've always loved a good shower, it was one of my favorite ways to relax. I also enjoyed shaving and some of the other prep work I did in the shower. So, I had a lot of reasons to enjoy it.
Naturally I shaved everything below my eyebrows. I did a once over on my face, but I’d shave that even closer when I got out. I made sure to use a nice moisturizing soap, I also took my time making sure to really soap up my ass, figuring that was probably going to get a bit of a workout, at least if Brad had his way. Well, okay, I was pretty excited about it, too. I almost kind of wished I had some outfits other than costumes to wear. I kind of felt like dressing up in something girly and fun and going into the store that way.
Other than my two costumes, I mostly just had panties and stockings. Really the few items I had were pretty slutty and while I doubted Brad, or Anna for that matter, would really care. I’d feel a bit weird riding the bus in a mini skirt and tube top. I wasn’t sure I was ready for that, yet, but it fueled me fingering my ass.
I stopped short again of actually playing with myself since I wanted to be fired up again for tonight. I did pull on a pair of black panties before putting my drab boy clothes on. I grabbed a backpack and tossed some of my girl clothes into it at the last moment. I thought maybe I could see about wearing some of it home. Maybe?
I arrived pretty early, but I figured that would give me time to get dressed and talk with Brad and Anna about whatever it was they wanted. The familiar bell over the door greeted me, though I was surprised no one was out front when I came in.
I heard a voice from the back call out, “Be out in a second!” A few moments later Anna stuck her head out and was about to do a greeting when she spotted me. “Oh, it's just you,” she said with a snooty accent.
I mocked a wound to my heart, “Really? You stab me with your words.”
“I’d rather stab you with something else,” she smirked and pantomimed stroking an imaginary cock.
I smiled, and blushed bright red. She smiled triumphantly and strolled over to the counter. I realized she was wearing a ringmaster costume as I regained my composure and walked over to her, “Brad mentioned you wanted to talk with me?”
She smiled mischievously for a moment, then said, “Yes, I was wondering which of us you were going to be taken by tonight?”
My eyes opened wide in surprise, my mouth opened but I couldn’t actually form any words. Anna jumped in first, “Don’t worry, I’m fine with you getting with Brad, I think it’s his turn anyway.” She laughed a little at my embarrassment. “Actually, I have a present for you,” she added in a much gentler tone.
“A present?” I said, still a little thrown off. “Do I dare ask?”
“Oh, I was just messing with you, don’t be such a sissy… so to speak,” she shook her head and laughed. “Sorry, not what I meant, I just… I realized some things about myself the other night thanks partly to you. Also, it occurred to me, you’re getting a nice collection of costumes, but you could use some other femme clothes, especially if you’re going on a job interview.”
I raised my eyebrows, but then it occurred to me, she and Brad probably talk all the time. She handed me a fairly large shopping bag. I opened it and looked inside, seeing a bunch of clothes. I looked up in surprise, “Wow! Anna, thank you.”
“You’re welcome, hun,” she grinned, then added excitedly, “I tried to get a mix of stuff, there’s some practical stuff, a nice suit, a sexy dress, some other fun stuff.”
“Wow! Where did you get all this?” I asked.
“I work in a costume shop, do you have any idea the amount of clothes I have access to?” she grinned.
I laughed, “I getcha, well thank you, this is awesome.”
I heard a girl’s voice from the back, “Anna, I got all the new costumes entered.” Jamie entered from the back, she was wearing a Flapper outfit that looked like it would be fun to wear. “Oh sorry, I didn’t know you were with a customer.”
Anna shook her head, “Actually this is our greeter for tonight.”
“Really?” Jamie looked surprised, “I thought the greeter tonight was Tiffany from the other night…” She then looked at me and her eyes narrowed. “Wait a second… that was you?” she asked.
I blushed a bit and nodded. Damn, was everyone out to embarrass the hell out of me?
“Cool, you make a really cute girl then! I hope you like tonight’s costume,” she added.
I perked up at that. “Oh, what is the costume?” I asked casually.
“You don’t know?” she asked. “Well, I don’t want to ruin the surprise.”
Dammit!
“That’s good,” added Brad entering the room. “She’ll get to see it soon enough! Good to see you,” he laughed a bit.
“Always good to be back,” I smiled, feeling a little awkward. I was already getting turned on, and I hadn’t even started dressing yet.
“Anna, did you get everything you needed?” Brad asked her.
“Yes, but I’ve got more, I’ll talk while I’m doing make-up, though,” she smiled at me.
“Great, come on back, we’ll get you started,” Brad waved me back.
“I can’t wait to see how you look!” Jamie said excitedly.
I blushed a little and followed Brad back into his office. He went over to the desk and picked up a box. He was smiling as he handed it to me. I looked and saw it was a… French Maid costume! Oh la la!
I looked up at Brad, my mouth open in surprise and he laughed, “I thought you’d be excited about this one.”
I nodded excitedly. “Absolutely, I can’t wait to try it on!”
“I can’t wait either,” Brad said and winked. “I’ll leave you to it. Hopefully you know where everything goes,” He winked again as he headed out.
He headed out of the office, and I grabbed the box to see what I was getting myself into this time.
I opened the box to get a better look. This wasn't some little one wear outfit, nope this was a heavy duty vinyl maid outfit. I rubbed the shiny material feeling myself getting aroused already. It was the traditional black and white French maid outfit with the white frilly parts done in a lighter, white vinyl, while the main dress was a heavier, thicker gauge of black vinyl. The skirt flared out widely, and looked like it was going to be quite short. The better to show off the black and white ruffled panties, I guess? Or maybe the black seamed stockings? The top showed off a fair amount of cleavage, but wasn't completely exposing. It did have short cap sleeves and came with some wrist length gloves, a white apron and little white cap, all in PVC. This looked like it was going to be amazing. Plus there was a heavy duty PVC corset, though that didn't look like it was a standard part of the costume. Nice to see I was getting the special treatment again.
I started stripping down while setting out the various pieces of the outfit. I was quickly in my little black panties, but those seemed tame in comparison to the ruffled ones.
I pulled mine down and quickly pulled on the ruffled panties, trying to tuck my rapidly hardening clit before it got fully erect. It hurt for a moment, but the pain helped me get control and I was able to tuck myself into the tight black underwear. The cool vinyl felt amazing and I was very much in heaven and getting really excited.
I picked up the dress and realized it was pretty heavy, so I decided to finish the undergarments first. I grabbed the stockings and rolled them up. Sliding the silky material up my legs, my head swam slightly as they gripped my shaved legs. My breath came short as my excitement spiked. I really debated jerking off quickly, but I wanted to be fresh for any fun later. I was really tempted though.
The stockings were designed as stay-ups, but I wanted more of an old school look. I dug around in my new bag that Anna gave me. Sure enough, I found a black garter belt and fastened it on. Feeling very sexy as I connected the garter tabs to the stocking tops. Connecting them around the stay up nubs was a bit of a pain, but I managed.
I then pulled out the corset, this really was heavy duty. I could feel the stays were very strong, probably even metal, and the PVC material meant this sucker wasn't going to have much give at all. I undid the laces and slid my portable prison on. It was very tight, I only had it slightly done and I was already out of breath. I got it positioned and tightened it enough that it wasn't going to fall down, then I started working on the laces. I knew I could only get them so tight, but I had a feeling my bosses were going to want this sucker tight.
I tied off the ends of the laces to the door handle and leaned in, feeling the bones squish me in and literally take my breath away. I untied the laces from the door, doing my best to tie them off behind me without having the lacing slip too much. It was pretty tight, but I knew it could go tighter. Though really getting it tighter both scared and thrilled me.
I dug around in my bag and found the nice silicone inserts from last time and slipped those into my corset cups. Between the falsies and the corset, I had some pretty nice tits. The cleavage shown by the dress would actually be some of mine!
I debated doing the dress, but I figured I should probably do make-up first. I pulled out the kit and set-up in front of the full length mirror in the office. Thankfully, the light was pretty good, so I was able to see myself clearly and had a good idea of how I wanted to go.
First, I put on foundation. This kit was pretty comprehensive, so it contained several colors and types of foundation. I found a nice match for my skin tone and applied a smooth base coat. I knew I wouldn't need too much since it was mostly dark out there. Just enough to keep a sheen off and hide any blemishes or anything.
By that same thought, it was going to be dark, so I knew I had to go kind of big with the make-up. The trick I'd found while practicing was being able to balance a big look without it looking like clown make-up. So, I started with the eyes; since the outfit was black and white, I wanted to put a splash of color in my make-up. I decided to go with red for the eye shadow. I know technically the make-up doesn't need to match the lipstick or anything, but it made things simpler for me if it all worked together. That's why I also just went with straight red. I'd been practicing blending colors, trying for a smoky effect and other cool things, but I wasn't ready to try them while being out yet.
I started from the inner part of the eye and carefully brushed on the bright red color. It was disorienting looking with one eye while holding the other closed. I guess that's why it's easier to have someone else do the make-up? Anyway, it took some time, but I was able to get the color to the shade I liked. I used my finger to smudge the edges and blend the color a bit, trying to get a nice faded look.
Once I was happy with the shadow, I moved to the mascara. This part always seemed so simple, but was deceptively complicated. It was just running the brush over your eyelashes, right? However, it was easy to get the mascara on your eyelid and mess up your eye shadow. And then trying to get that off screwed up your whole look. Believe me, I'd been practicing enough that I'd done all of them. The tough part was getting it all over without clumping, and I managed that pretty well. Like I said, it was going to be dark, so mascara was a bit extra for this. I pulled out the liquid eye liner and ran a quick line across the bottom of my lower eyelid. It was a real pain in the ass to do, but I managed it. It helped highlight the look, so I decided it was worth the irritation.
Next, doing some blush was fairly easy. Using the large brush, I put a bit of red on my cheeks. The trick was to blend it all out so it didn't look like you had red splotches, just a nice color highlight. Then onto the lips. This was also deceptively easy. I found it was really easy to go too big and look freakish. I wet my lips and filled in the outline of the lip, covering the whole natural area getting a nice reddish look. I debated putting on some lip gloss or lip liner, but again figured that was a bit much.
I took a look in the mirror and smiled at myself. I looked pretty good, and I managed it myself. I blew myself a kiss and began digging in my bag for a wig. I was trying to decide between the two I had when there was a knock on the door. I absentmindedly answered and kept digging in my bag.
“Ready for your make-up… oh?” Anna said, then trailed off as I looked up. “You already did your make-up?”
I smiled, “Yeah, how does it look?” I screwed up my face, waiting to hear it was terrible.
“Pretty good actually. I probably would have gone a little heavier, but I guess if you're just out on the street, it doesn't really matter.”
“That's kind of what I was thinking,” I said, holding the blonde and black wigs in my hands. “Which do you think goes better with this outfit?”
“I think we should keep going with the red theme,” she said, holding out a red wig. I realized this one was very long, probably at least shoulder length, maybe even longer. My mouth came open in surprise. I'm not sure why, this was a costume shop, they had a ton of stuff, but it was just another dream come true for me. Now I got to be a red-head!
I took the wig and settled it on, Anna helped me, getting uncomfortably close. I could feel the heat from her breath on my neck and her breasts gently rubbing against my shoulder. As we got the wig settled to a nice location, Anna whispered in my ear, “I like the garters, nice touch.” She reached down and plucked one of the straps, snapping it against my skin.
My breath caught as I gasped in excitement and my clit surged in my panties. “Hey, I'm already worked up, teasing like that is not nice,” I grinned.
Anna just chuckled evilly and said, “I know. How about I take your breath away?”
“I… wha…” I started to ask, then she pulled on the laces for the corset, and my breath was squished out of me. She tugged on the strings for a few minutes before getting everything nice and settled and retying the back laces.
She then turned and started heading out, calling over her shoulder, “I was going to tell you a surprise while doing your make-up, but I guess you'll just have to wait. Oh, and Brad left shoes on the desk for you.”
I looked back at the desk, I hadn't noticed them but she was right. There was a pair of white and black pumps, I believe they were called saddle shoes. These had a super high heel, probably at least five, maybe six inches. Good thing I'd been practicing walking in heels, too.
I figured I should get the rest of the dress on, not that it seemed anyone would be upset if I pranced around in my underwear. So, I pulled out the dress itself, I undid the zip in the back and realized that was probably going to be a pain in the ass to do by myself. I slid the cool, slick PVC over my head and let it drop down, tugging the tighter part down to my waist, I could feel how wide the skirt flared out. As it settled I realized there was some kind of built-in petticoat or something causing it to flair. I slipped my arms through the shoulders and settled the collar around my tits. I struggled a little getting the zipper done, especially with how limited my mobility was from the corset, but I eventually got the zip all the way up.
I reached back into the box, and pulled out the little apron and tied it around my waist. It was cute and the splash of white helped offset the mostly black uniform. I pulled out the little cap and looked it over. I wasn't completely clear on how it fastened to my hair, but I figured I should do that before heading out. I gave it my best, but it didn't quite sit right, so I'd have to ask about that.
I took the shoes and sat down to slip these on. Good thing I waited, these were really high heels. Holy hell, I couldn't believe it! I stood and felt like I was on stilts. Even with all my practice this was going to be a challenge.
I tottered back over to the desk, focusing on keeping my hips centered over the shoes. I picked up the gloves and slid them on. These were also PVC, but much shorter than the elbow length gloves from last time. Instead these just came slightly past the wrist and then the white flared out. They again gave a nice pop of color.
I looked myself over in the mirror, and man did I look like sex on heels! I couldn't believe the sexpot in the mirror was me. It made me feel really confident about going out this time. So, I turned and headed out of the office. I came into the stockroom area and saw Jamie was working on some boxes and items. She looked over and whistled, “Wow, you look fantastic!”
“This old thing?” I asked, waving her off. “Really, though, thank you, that makes me feel better about going out.”
“Girl, you're gonna knock 'em dead. You'll probably have job offers to come and be someone's maid. Maybe even some marriage offers!” She laughed and winked, settling back into her work, but stealing a quick glance as she did.
The door swung open and Brad came into the back, “Did you need something, Jamie?” He then spotted me and his jaw fell open. “Wow!” was all he could manage to say.
I struck a pose, smiling and blinking. “So, it looks good then?” I asked.
He just nodded dumbfounded. He came over and took my hand, leading me out to the front. He must have recovered a bit since he leaned through the door and said to Anna, “Hey Anna, may I present our greeter for the night!” And pulled me through the door.
I struck a pose again and Anna just shook her head, “Even with the preview I had, you really have surprised me again.”
Brad nodded, probably not realizing he was still holding my hand, and I didn't really feel like breaking contact. Brad added, “You really outdid yourself, Anna. Her make-up looks amazing.”
“Actually,” Anna interjected, “She did her own make-up.”
“She did, did she?” Brad asked, though more to me than Anna.
I smiled and nodded and said in my best femme voice, “She sure did, but I had a good teacher.” I gave Anna a knowing wink.
“She is great, that's why it's going to be tough running things without her,” he added, letting go of my hand somewhat reluctantly.
“What do you mean without her?” I asked suddenly.
“Oh, she didn't tell you? Anna gave her notice, she'll be done in two weeks,” Brad said matter-of-factually.
I looked at Anna and raised my eyebrow questioningly. I realized this must have been what she was going to tell me while doing my make-up. Anna shrugged, “Well, I guess you got some of the surprise. I'll fill you in on the rest later.”
Brad interrupted, “Sorry, but we do need to get you started, Tiff.” I had a little momentary thrill as Brad called me by my girl name that made me forget about my confusion.
“Okay, we can talk more after,” I said to both Anna and Brad. “Oh, I wasn't sure about this cap and how to secure it. Could you show me?”
Brad showed me how the fastener worked, but he went ahead and fastened it on me. As he did so, he brushed up against me, I could feel his hard cock. I had to bite my lip to keep myself from rubbing him. Anna just smiled knowingly at me. My cheeks flushed, as if I wasn't aroused enough already.
We made our way outside, Brad wrapping his arm around me. I wasn't sure how much he was helping with the heels and how much just being close, either way it felt quite nice. We got to the sidewalk and Brad somewhat hesitantly let me go, handing the sign over to me. He smiled as he looked me up and down, “Damn, you really are amazing!”
“Awww, thanks sweetie!” I leaned in and kissed him on the cheek. I'm not sure why, I guess I wanted to do more, but knew we couldn't, at least not right now.
Brad smiled wider as I rubbed the lipstick off his cheek. “You need anything else?” he asked.
I smiled slyly and said, “I do, but we'll have to wait for that,” I winked and turned to the passing cars. Already a few had honked. So, I waved back. Brad just shook his head and trekked back inside.
The shift passed very quickly again. It was amazing just how into playing it up, I could get. Between waving to cars, posing for pictures, getting several phone numbers and e-mail addresses, not to mention offers for dates and yes, even a marriage proposal, I was in sissy maid heaven. The big event happened after about an hour or so into the shift.
Several cars had pulled in, with guys getting out and coming over to talk to me, however the one an hour into the shift was a bit different. First, he was wearing a suit, no tie, but he was also tall, confident and pretty good looking. He approached me and stood watching for a moment. So, I posed thinking he was going to take a picture.
Instead he said, “Hello, I'm Darien Davis, we have an appointment to meet in a couple days, but I wanted to meet you beforehand.”
My mind blanked for a moment… who? Appointment? What the hell was he talking about? Ohhhhh! This was the boss. Brad's boss specifically. I recovered somewhat, “Oh hello, it's nice to meet you!”
It wasn't exactly witty repartee, but it covered the fact that I had no idea what to say. Also, I wasn't sure how he'd react to me being a cross dresser. I know attitudes were changing with that, but this was a company and a business. As I got a closer look, he was really good looking. Not like male-model pretty, more rugged or dashing, but definitely turn and check him out again, good looking.
“Well, its great to meet you. You've only been at this a couple times, but everyone has raved. Especially Brad and Anna,” Darien explained.
“Well, they've been super sweet and have been really showing me the ropes,” I smiled brightly. I almost added 'so to speak', but didn't really want to explain all the sexual liaisons I'd had with the staff.
He smiled back, and he had an odd look, like he saw something, but wasn't sure. Had I been 'made'? One thing about trying to pass as female, is when someone realizes you're not. This is being made, and I thought maybe he'd figured it out, but then he smiled warmly again. “Yeah, they've been a good crew, we'll miss Anna, too. I was hoping she'd move up to manage her own store soon, but seems she's got other plans.”
I nodded, “Yes, she told me a little, but we didn't have much time to talk about it.”
“Well, you look like you're busy, so I'll let you get back to it,” he gestured to the traffic.
“As you like, you're paying me, so I probably should get to work,” I joked with him.
He smiled, shaking his head a bit, he then took my hand and kissed the back of it. Holy hell! I didn't think guys really did shit like that? But the gesture, as outdated and ridiculous as it was, really hit me. I was so excited to be treated like a lady, that I actually squirted a little. Yeah, I know, not very lady-like, but I'd only been a lady for a couple hours.
I could only gasp slightly for air as he did that. So, he added, “You really look amazing. I look forward to having you in my office.”
I smiled and nodded, “I'm looking forward to being had.”
He held my hand just a bit longer, and seemed reluctant to let go, but he did eventually. Then headed inside. Well, the shift had been a breeze up until that point. And by breeze, I mean the highly flared skirt just let any and all cold breezes right up there, so even though I was creaming my panties most of the time, it also got pretty chilly where I was.
So, after Darien introduced himself, the rest of the shift passed in a daze and it wasn't long before Brad was back out to recover me. When he walked up, I looked surprised, “Wow! Already?”
“Already? You were done about 10 minutes ago, Anna and I had a bet on whether you'd realize on your own… I lost,” he added.
“Oh, yeah, I'm just… enjoying playing it up out here. I guess I like showing off?” I shrugged, not sure and not really caring to be honest.
Brad reached over to take the sign, “Well, we're closing in just a bit, so unless you're planning to go home dressed in costume…”
I looked thoughtfully, “I wonder how this would go on the bus?”
“The bus? Most folks probably wouldn't even notice!” he joked.
I shrugged and took his arm and we started walking back in.
“Would you really wear that home?” he asked.
I shrugged, “I guess so, I mean, I've always wanted to try going out as a girl, but I've never really had the guts, or anywhere to go.”
“What about Sixth Street?” Brad asked.
“The gay bar? I dunno, I guess I figured it was always just guys, so…” I shrugged.
“Would you want to go?” Brad asked, raising his eyebrows.
I looked surprised, “You mean, to say, tonight?”
Brad shrugged, “I don't know, maybe, I was just thinking, it might be fun.”
I smiled mischievously and leaned in closer, “What about any… extra-curricular activities?”
“We could still do whatever, we'd either have to come back, go to one of our places… something,” Brad smiled brightly.
“Oh, you want to show off your hot piece of ass? Is that it?” I teased.
“I'll admit, it would be pretty awesome to be seen with you on my arm,” Brad teased back.
“And being on your arm would make me a lot less nervous going out,” I emphasized 'a lot'.
Our conversation was interrupted as we re-entered the store. Anna looked up as the bell dinged, she looked ready to tell the customer they were about to close when she saw us. She was just about to go back to her work, when she looked at me leaning on Brad's arm and gave me a little eyebrow raise. I just shrugged and smiled.
Everything went to their usual routine, Anna, Jamie and Brad went about closing while I headed back into the office to take off my shoes and sit down for a few minutes. I took advantage of this time to start going through some of the items that Anna gave me in the bag and see if there were any good outfits. I was getting a good inventory when I hit a couple of solid items that I first thought might be shoes. I pulled them out and realized they were a bag with a… holy shit! A dildo, butt plug and tub of lube. Wow! Anna really did think of everything.
I thought for a few minutes and decided. I quickly took the plug and the lube into the bathroom. I nervously pulled out the plug from the pack, looking at the tapered shape and flared base and wondered briefly if it was going to fit. Well, only one way to find out.
I took a generous amount of lube and greased up my ass. Sliding the first part of the plug in was a strange sensation, the cool smoothness slid in easily to a point, then it hit some resistance and my ass really started to open up. I hit a point where I had to ease off and start basically fucking myself with the plug, then I opened up and the rest of it slid home. My ass closed around the flared base and I couldn't believe how full I felt.
I stood up and was amazed at how difficult it was going to be to walk with this up my ass. Maybe this wasn't such a good idea? I decided to give it a few minutes and see how I felt. I could always take it back out.
As I started walking, the combination of the plug and the heels really had me swaying my hips and focusing on my walking. I began really focusing on my posture, not that I had much choice with the corset on. Anyway, I made it quickly back in the office and sat on the couch. The short walk helped me get comfortable with my new friend. So comfortable, that when I sat down I sat right on the plug in my ass. I almost yelped and jumped, instead I sat leaning to one side. Sitting definitely put a lot more pressure on the plug, making me very aware of it.
Brad came in a few minutes later. “Hey, I… oh wow,” he started, then fumbled as he caught sight of me.
“What?” I looked confused.
He grinned, “Nothing, I just thought you might have started getting changed.”
“Oh,” I looked a little embarrassed, “I thought you might want to… check it out more.”
Brad smiled, “I do! Can I get a pic?”
As he held up his phone, I told him, “Only if you send me copies!”
I posed and he took several pics. He then sat on the couch, and I sat next to him. I was very aware of my plug and how horny I was. Brad kissed me, softly and tenderly at first, but then quickly he kissed me hard and I kissed him back. It only took a moment before his hands were exploring my body. One was rubbing my stockinged thigh, the other tracing the bones in my corset. I leaned in, feeling the heat radiating off his body. In this position, I couldn't really move my hands much, so I put one arm around his back and just held on, enjoying the sensations of his mouth and his hands.
He moved his mouth down to kiss my neck and I wrapped my fingers in his hair, moaning loudly as he nibbled on my skin, sending little electric sparks along my skin. He kissed around on me for several minutes, moving up to nibble on my ear, then back down to my neck, just driving me completely wild. As much as I wanted this to keep going on, I was getting out of my mind with lust and needed him soon.
I slid my hand down from his hair, running it over his chest and down his stomach to his crotch. I could feel his cock was rock hard and I wanted it bad. As I rubbed it through his pants, he started making grunting sounds while kissing my neck.
So, I rubbed the whole length hard, feeling him groan through my neck. I unbuttoned his pants and slid my hand in, he scooted up and I slid his pants and underwear off. I took his hard cock in my hand, stroking it softly, seeing how excited he was. As I was doing this, he started kissing my neck again. This got me moaning and stroking him harder, which got him nibbling and sucking on my neck more, and we got into this hot cycle of teasing and exciting each other.
After a few minutes, I couldn't take any more and leaned forward to lick his cock head. He groaned and I slid my legs onto the couch, so I could really get down and suck him. He sat back and began playing with my legs with one hand. The other stroked my wig gently.
I took my time, making a nice, long slow production, getting him very worked up. Licking from the tip down to the balls, teasing them, feeling how heavy and full they were. Licking back up, working my tongue the whole way. It only took a few minutes before his hands slid up my legs, lifting the short skirt and he started playing with ass.
I looked up and smiled with a twinkle in my eye, “You might find a little… friend… back there.” I smiled and went back to licking and slurping on his cock. He just raised his eyebrow and traced his hand along my panties, making me shudder with pleasure.
His exploring found the base of the butt plug a moment later, “What is this?” he asked. He leaned over a bit to get a good look, as he pulled the thong aside and said, “Oh my!” He started playing with the plug and I started making all kinds of purring and groaning sounds. Needless to say, that just encouraged him more.
I lost my focus on sucking him as the pleasure in my ass took over. He'd pull the plug out slightly, letting it slip back into my ass, fucking me with the plug. I simply laid on his lap, moaning and squirming as he teased my toy.
“You are a really bad girl,” he stated. I looked up and he was smiling like he just won a jackpot. I tried to answer but could only manage brief gasping and moaning. “I mean you'd have to be a real slut to wear something like this under a French maid dress.”
I squirted a little when he called me a slut. I really was, and the amazing part was I didn't care. “Are you a dirty little slut, Tiffany?”
I nodded, “Oh my, yes!”
“What does my little slut want?” he asked, pulling the plug all the way out.
“Oh my!” I grasped his cock. “I want you in me,” I moaned, stroking him.
He pulled me up, and sat me on his lap. I reached back and lined him up with my asshole. Thankfully, I was very lubed from the toy, so his head slipped right in. I gasped again and moaned as I sank slowly down on him, feeling every inch slide into me. I shuddered in pleasure as he moaned his pleasure.
I stopped for a moment, letting my ass adjust to being so full again. I looked at him, “Was it worth the wait?” in my best sexy whisper.
“Oh fuck, yes,” he replied, running his hands down my corseted side down to my stockinged legs. I gave a little shudder of pleasure as I slowly slid up, feeling his cock sliding out was such a delicious feeling. As I got about half of him out, I slid back down moaning the whole way. I stopped again, but just to catch my breath.
I bounced back up, starting into a nice slow pace, riding his rock hardness. My own hardness was straining the front of my panties, I was so aroused, I thought they might rip. I debated pulling myself out, but I was just lost in the haze of pleasure coming from my ass. I didn't really want to lose that focus right now.
Instead after a few minutes, I wanted to really get fucked. I leaned into Brad's ear, “Do you want to fuck me?”
“I thought I was fucking you?” he smiled back.
“I mean change position,” I moaned somewhat desperately.
“How do you want to be?”
“I don't give a damn, I just want you to plow the hell out of me,” I breathed raggedly.
Brad pushed me up, I climbed up. He reached up and unzipped the back of the dress, and I let it fall off my shoulders and bunch up on the floor. Brad pulled me in and kissed me hard, as he bit my neck, he moved me over to his desk. I was about to ask what we were doing, when he spun me around and bent me over the desk. As I leaned down, I felt him slide up behind me and line his cock up with my ass. He thrust in and went balls deep in one stroke. I gasped and moaned at the same time, and before I could fully recover he was sliding in and out with long, slow strokes. He pulled most of the way out, teasing me, before sliding deep back in.
“What did you want, my little slut?” Brad asked, pulling most of the way out.
“Fuck me, please fuck me hard,” I begged, pushing my ass, trying to get him back in me.
Brad took pity on me and began fucking me, and I mean fucking me really hard. The sensation was almost overwhelming. The sounds of flesh smacking combined with the feel of his dick sliding in and out of me had me clawing at the desk.
“Ohhh, I think she likes it,” he growled without slowing down.
I nodded vigorously, “Oh hell, yes! You can fuck me like this any time!”
“Really? Any time?” Brad asked.
“Yes, just please don't slow down,” I begged.
“I'm gonna cum soon, we keep going like this,” Brad laughed.
“Oooh, you gonna cum in me?” I teased.
“You want me to cum in you?” he asked, picking up his pace.
“Oh fuck, yes! Fill me up with your hot cum! Breed my sissy ass,” I half-moaned, half-begged.
I slid my hand down into my panties, diddling myself. I was so worked up, I was pretty sure I was going to cum in an instant. Me playing with myself, seemed to fire Brad up even more. He really picked up the pace, absolutely slamming into my ass. My moans were pretty steady and I could feel the orgasm building up in me, it felt strange though, different. I could only guess it was the rubbing on my prostate that was making this build up differently. That or the excitement of him cumming in me. I'm not sure why that idea turned me on so much, but it really did.
Brad began groaning, so I picked up diddling myself and in just a few moments, I was arching and starting to spasm on his cock. I began pushing back, trying to get more sensation before I shuddered and screamed, shooting my girl cream in my panties.
My orgasm made my ass tighten up and Brad moaned loudly, grabbing tightly onto my hips and pulling me deep on his cock. I could feel him spasm and he thrust several times as his cock pulsed and shot his load into me. It was such a strange sensation, but I loved it. I started humping slowly, milking the last bits of cum and Brad's orgasm as I panted for breath.
“Holy shit,” was all Brad could manage to say.
I smiled proudly, teasing, “I think he likes it!”
Brad chuckled, “That was fucking mind-blowing… wow.”
“That was amazing,” I agreed.
Brad leaned down to trail kisses down my spine, making me shudder. I could feel him starting to shrink and after a few moments he slipped out. “Oohhh,” I moaned, disappointed.
“Sorry, babe. Gotta come out eventually,” Brad said.
“I know, I'd just… gotten used to being filled. I feel… kinda empty,” I said.
Brad chuckled, “Well, hang on a second. I can fix that.” I could hear him step away. I turned my head to the side, looking back as best as I could since I was still laying on the desk. I was trying to stand up, but my legs felt pretty wobbly and I didn't trust my wobbly legs on the heels. Brad stepped back over a moment later, and started playing with my ass.
“Oooooh, you ready to go again?” I smiled.
Brad held up the butt plug and started teasing my asshole, making me gasp suddenly. Then I moaned as he slid the plug back into me. I shuddered as the plug slid right in all the way to the base with no problems this time. I guess my slutty ass was all stretched out.
“Feel full again?” Brad asked.
I nodded, biting my lip as I could feel my libido rising back up. My clit was starting to get hard again, so I tucked it back into my panties, and got them lined up properly, pulling the thong around the base of the plug. I stood and I was a little wobbly. Between the heels, being bent over and fucked, then being plugged, I had gone through a workout.
I turned and Brad was smiling down at me, “What?” I asked, cocking my head to the side.
He looked me up and down in the corset, garters, stockings and heels, “My goodness, you are sexy.” He pulled me into his arms and started kissing me. I melted into his arms, amazed at how nice it felt. I was also surprised at how aroused I was getting. I still had a sticky mess all inside my panties with how excited I was the previous time.
Brad broke the kiss, “Do you want to sit for a bit?”
I nodded and we slid over to the couch, I made the mistake of forgetting the plug and sitting directly on that sucker, again. A moment later I tucked my legs on the couch and was snuggled up, my head on Brad's shoulder. This was pretty nice, too.
Brad wrapped his arm around me, and we both sat there quietly for a bit. I may have dozed off, because I started a moment later when he asked me something.
“I'm sorry, what?” I asked.
“You want to get changed? I can step out for a few minutes,” he offered.
I thought for a moment, “No, I'm just going to wear this home.”
“This?” Brad asked, looking pointedly at my panties, stockings and corset combination.
“Well, I'm going to put something over top, obviously,” I noted.
“Good, I wouldn't want you getting arrested!” Brad joked.
I leaned up and kissed him on the cheek, “Thanks for looking out. Speaking of looking, I'm going to try on some of this stuff Anna gave me. Do you want to watch?” I smiled and raised my eyebrows.
Brad looked like he just won a prize, “Hell, yes! What kind of stuff did she get?”
“I don't know, I didn't really get to go through it much,” I pulled out a few pieces. The business suit caught my eye, but I didn't really want to mess with anything complicated right now, plus I was looking for something a little… well, sluttier, if I'm being honest. For some reason, the idea of riding the bus home looking like a hooker had me getting very fired up again. If my panties weren't already wet, I'd be making them wet.
So, I dug around and found a denim mini-skirt that was cute and kinda sexy. Not really what I was going for, but it might not be a bad start. So, I shimmied into that and buttoned it up, doing the zipper in the back. I looked in the mirror and turned to Brad. He smiled and nodded.
“Not bad,” I said, shrugging.
“It looks good, but you don't seem impressed,” Brad noted.
I shrugged, “It's not bad, but not exactly what I was looking for.”
“So, what are you looking for?” Brad asked.
“I dunno, I guess something sexier,” I shrugged again, digging in the bag. Then I hit it, a pleather mini-skirt! Aha! Pulling it out of the bag, I smiled at Brad.
“Find something?” he asked.
I answered by undoing the jean skirt and dropping it. Then I pulled on the fake leather skirt… oh yeah! This felt nice and it was really short. Like dangerously, so. I felt like a total slutty bad-ass pulling this one on. I was so wrapped up in checking myself out, it took me a moment to realize that Brad was really checking me out.
I started gyrating my hips, purposefully looking at Brad in the mirror. He smiled and shook his head as he started adjusting his cock in his pants.
“Everything okay back there?” I smiled.
“It's great!” he replied. “The view certainly couldn't be better.”
I dug around trying to find a top. It looked like most of the items had a top and bottom that Anna had, very thoughtfully, tried to pair together for me. What the heck did she intend to do with this? I found a few tops that were either low-cut, tight or some combination of both, and then I found the pleather bustier. I wasn't sure how well this type of top would work with the corset, but fuck it. I had to see this look. It took me a few moments to get the top zipped on the right way, but when I did and looked, oh man. I looked hot. Well, I looked like a cheap whore for rent, but let's be fair, that's the look I was going for!
I turned to Brad and strolled slowly over to him, tossing my hair to the side, “What do you think?”
“It's very sexy! You look really hot!” he was eyeing me up and down. That was a real thrill for him to be eyeing me up, considering he'd been fucking the hell out of me just ten minutes earlier.
I bit my lip, “You don't think it's too much?”
“Well, yeah, it's way too much, but that's what makes it thrilling, right?”
I answered by gyrating my hips and then grinding down, putting my ass right in his face. He only took a moment before his hands were all over my ass. This got me grinding even more. I turned and straddled his lap, wrapping my arms around his neck and kissing him again.
“Damn girl, you want to go again?” he asked at a break.
I nodded an emphatic yes, “Do you?”
He shrugged, “I wanted to see if you wanted to go out.”
“To Sixth Street?” I asked. His turn to nod yes. I looked thoughtfully, a chance to go to a trans friendly bar decked out like a total slut with a guy on my arm? Sign me up! “Abso-fucking-lutely! Can you give me ten minutes to fix my make-up? Oh and do you have more of these panties?”
“Yeah, we have a bunch, what's wrong with those?” he replied.
“Well, other than me cumming in them and your cum leaking out of me into them, nothing. I'd just hate to leave a puddle anywhere I sit at the bar.”
Brad laughed and I slid off to let him go find me some new underwear. In the meantime, I pulled out the make-up kit and set about working on fixing my look. I wanted to still go full slut, but I didn't have time to do much but fix and re-apply.
Brad came back in as I was finishing up. I stood and did little spin as he entered. He handed me a new pair of panties. I pulled the old ones off, and was amazed at the puddle of cum in them.
I folded them up and put them in an empty plastic bag, hopefully they would stay wrapped up in my backpack and I could clean them later.
He just whistled and smiled, “You ready to go?”
I nodded, then I thought about it, “Oh shit, I guess I need to put stuff in my purse?”
Brad laughed, “You girls take forever to get ready.”
“Hey, it takes a lot of time to look this cheap!” I stuck my tongue out at him.
I pretended to punch him in the arm. Instead I grabbed my wallet and some make-up and a few other things and tossed them in the small purse Anna had thoughtfully included. I slung the leather bag over my shoulder and took Brad's arm. He thoughtfully took my backpack with us, too.
We walked out and I immediately shivered with the small amount of clothing and the cold air. Brad took off his coat and wrapped it around me. It was such a gentlemanly thing to do. I smiled warmly at him, and he just shrugged. I guess I was going to have to get a few more girl accessories. Note to self: get a coat for the cold.
We climbed into the car and Brad drove us over to Sixth Street. It was only about ten minutes away, though this late on a Friday, the traffic had thinned out, so it was a nice quick ride.
We parked and my stomach suddenly felt like I had butterflies. Why the hell was I so nervous now? I'd been parading around in a French Maid costume on the side of the street for hours. Now, I was just getting ready to walk into a bar, so no big deal, right?
Brad must have noticed my hesitation, “Hey, you okay?”
I nodded, “Yeah, I think so, just… I don't even know, a wave of like, fear. I guess.” I held up my hand and it was shaking a little.
“Well, we don't have to go in if you don't want to. I thought it would be fun for you,” he sounded genuinely concerned. It was kind of sweet, actually.
“No, it's good, I want to go,” I smiled. “I think I'm okay, just some kind of irrational fear, I guess? I don't know.”
“Yeah, I would think this would be a cakewalk after doing the costume on the side of the road?”
I laughed, “That's exactly what I was thinking.”
“Do you want to talk about it?” Brad took my hand. Okay, that sweet gesture had me creaming my panties again, and that started getting me aroused again. And getting horny took away any trace of fear.
I smiled and leaned, kissing him softly on the cheek, “No, I want to get a drink.” I held up my hand which was nice and steady again.
We walked into Sixth Street and the place was bustling. I did have a few moments with the butterflies returning, but they passed quickly. I took off the coat and handed it back to Brad. I could feel a number of eyes turn my way, and several soft comments were made, too. I did a quick hair flip and adjusted my purse strap. I kinda wished I was wearing something even more outrageous now. I wondered what could be more provocative, but not get me arrested?
Brad hung up his coat and took my arm, guiding me into the bar area. I made sure to put an extra emphasis on swinging my hips and strutting my stuff. “Do you want to sit at the bar?” he asked.
“I don't know, I've never been here, I'll follow you,” I replied.
So, Brad took us into the bar area and found a small high table off to the side, but still near the main bar. I slid into the seat, and my already short skirt rode up even more. I didn't bother to adjust it back down, either. My goodness, I felt like a wanton slut. Of course, it was probably the butt plug buried in my ass that was really getting me turned on. It might have also been all the guys, and okay, some of the girls, checking me out.
After making sure I was seated, Brad said, “You want a drink? I'll grab us something?”
“Sure! Please get a water, too,” I said, realizing all of our 'exercise' earlier and now my excitement and nervousness were making me really thirsty.
I sat checking the place out while he was at the bar. It was a pretty standard brew pub-y, sports bar kind of place. Of course, since it was mostly a gay bar, there were mostly same sex couples, but also some boy-girl couples. Though I then wondered if there were any other trans girls here? I saw some posters and realized there was a drag night coming up. Thankfully, Brad was quick and set a glass of wine down in front of me, along with a glass of water.
He sat down, “So, what do you think?”
“It's nice, looks like a pretty standard pub-type place,” I noted, taking a sip of the wine. It was a red wine, so it was kind of sweet. Good thing, because I'm not really a big drinker and don't generally like alcohol that much.
“Yeah, but the clientele are a little more sexually open,” he added.
“Good point, I did notice that,” I smiled.
Brad laughed, “Have you seen all the folks checking you out?”
I blushed and laughed a little, taking another sip, “Yeah, I sort of noticed that… looks like I'm popular.”
“Well, you make amazing eye candy, and your choice of outfit is…” Brad thought.
“Slutty?” I interrupted.
Brad laughed, “Well, yeah. I was going to say eye-catching… though slutty does fit too.”
“I believe in truth in advertising,” I winked, feeling my tuck dripping into my panties again.
“Oh, so just a couple days as a girl and you're a slut?”
“Well, I sucked and fucked you, before we went on a date, I might add.”
Brad nodded, “Okay, but that just means you're adventurous and open.”
“My panties are soaked from how fucking turned on I am right now,” I said, blushing again. Brad was about to say something, when I added, “I have a butt plug in and I wish I was wearing something even more provocative.” I bit my lip. Dammit! I was so fucking horny now, I just wanted him to throw me over the table and start fucking me. Well, okay the table was kind of high, maybe the stool? Oh, who gives a shit, I wanted cock and I wanted it right now.
“I… wow… how much more provocative you wanna get?” was all Brad could coherently manage.
“Thigh high boots?” I smiled and bit my lip.
“Damn! Really? … I can do that, you know?” he added.
“Ohh! Really?” Yes, I creamed my panties on that one.
Brad nodded, “We don't have a ton of them, but we have some.”
“And you're just telling me this, now?” I asked.
Brad laughed, “Well, you seemed a bit nervous about going out, so I didn't want you to feel pressured or anything.”
“So, I could try some on later?” I asked breathlessly.
“Oh yeah, I have a pair in my office I was hoping you'd like. They should be your size,” he stated, taking a sip of his drink.
I squirted a little in my panties with that. “So, you were already planning that? …Do you wanna fuck me?” I asked breathlessly.
“Right now?” Brad asked, almost choking on his beer.
I nodded as I squirted more. Heaven help me, I was so fucking horny. I wanted to jump him right then and there.
“We could go back to the office,” Brad shrugged.
I shook my head, “Is there someplace here we can go?” I looked around the bar.
“Not really, not without getting caught anyway,” Brad added.
“Got to be honest, I don't really care. We can go in the alley, or the car, but I need it now, or I at least need to take this plug out,” I added.
Brad looked around, “Well, there is one place, we can go, that's right nearby.”
“Really?” I finished my drink quickly, feeling the wine hit my head a moment later.
“Yeah, it's not exactly nice…” he trailed off.
I looked up and urgently whispered, “I don't care, I need you now!”
Brad wasn't going to argue, he finished his beer and stood, helping me off the stool. I took his arm as we headed back out, only stopping for a moment to grab his coat. We walked a little down the block, each step like a spike, driving my desire higher and higher. Feeling Brad next me, the sound of my heels clicking on the pavement, the eyes of everyone passing me and the plug making itself known with every step; these all had me leaking so much, it felt like I was peeing myself.
I didn't really pay much attention when we went into the place, it registered in the back of my head that there were racks of movies and sex toys on shelves, but I was kind of single-minded at that point and didn't notice when we went through a doorway into a dark hallway and a series of doors with lights over them. Brad pulled me towards one, and he slid us into a small booth. He set me down on a small bench and turned to mess around with a small TV screen in the wall.
He was playing with something, so I started playing with his cock through his pants. As I thought, he was pretty worked up and I could feel his already hard cock absolutely throbbing. I undid his pants and pulled out his cock, wasting no time I wrapped my lips around and started sucking him deep.
“Oh shit!” he stammered as the TV flared to life. He stepped back and let me get better access to his cock. I was sucking like this was my last meal. I was so wrapped up in enjoying my treat, I didn't really notice what was on the TV until I heard the moaning that sounded like it was mirroring my lust.
I took a breath and looked over to see a really hot trans girl sucking on two guys' cocks. Holy shit, this was hardcore porn! Where the fuck did he take me? Not that I was upset, far from it. This was driving me further up the wall, and I was already pretty far up there. I guessed we were in an adult bookstore, or something along those lines.
“You like it?” Brad asked as he ran his hand along my head.
I nodded, “Fuck yes! That's hot as hell!” I started sucking him again, pulling him to the side, so I could watch the screen while sucking him.
I blew him like that for several minutes when the scene in the porn changed. One guy moved down to slide his cock in the trans girl's ass, while she focused on really sucking the other guy. That made me remember my plug and what I really wanted.
I looked up, “You want to take me again?”
He answered by sitting on the bench and pulling me onto his lap, facing away from him. My skirt was so short, it was already partly hiked up. I just needed to pull my thong to the side and slip out my plug. I lined his cock up with my ass and he pretty much slid all the way on the first try.
“Oh fuck!” I yelled, shuddering and trying to get my brain working. My mind was blank, all I could do was watch the hot blonde trans getting railed while my lover's cock was buried all the way in me. He gave me a moment to adjust and to catch my breath.
While I was catching my breath, he leaned and whispered in my ear, “Looks like she's loving all that attention.”
I nodded, “Oh fuck yes, that is soooo fucking hot!”
I started sliding up and down, amazed at how good it felt. Feeling every inch of him sliding in and out was finally scratching that itch for me. Of course, now I could feel it building up again, so I started really riding him.
“So, would you like that?”
“To get tag teamed? Fuck, yes!” I moaned, picking up my pace and my clit was almost hard again. I was a little surprised, I was usually one and done. Then again, I hadn't been this turned on in a long time. Brad dirty talking was getting me even more worked up. “That must feel amazing, to be full at both ends!”
“You really are a slut, then?” he teased.
“Oh hell yes! I am a complete fucking slut!” I was bouncing on his cock for all I was worth, he was lifting me up, too. Helping me to really drive down on him. We kept going like that for some time, me moaning and him talking dirty in my ear. Calling me all sorts of dirty names, saying how hot I'd look with cocks in both holes. I was so over the top aroused, I wanted to play with myself, but I didn't want this to end either.
The trio on the screen, changed up and the girl was spun around, the guys getting a shot at the other hole. It did occur to me, she was now sucking the cock that had just been up her ass. Wow! That was at the same time kinda gross and super fucking hot, “Oh fuck, that's hot!” I moaned.
“What? Changing up? You like sucking the cock that's just been up your ass?” Brad asked.
“I don't know, let's see,” I replied over my shoulder. I stood up off his cock and knelt down in front of him, quickly taking his cock in my mouth.
“Oh damn…” Brad gasped as I started sucking hard and fast. There was that brief thought that his dick had just been deep in my ass and what might be all over it, but for some reason that thought just made me feel even sluttier.
I wondered what else I was willing to do? The answer scared me a little, that short of serious bodily harm, I couldn't really come up with much.
Brad looked down, biting his lip and breathing heavily, clearly very worked up at what a slut I was being. He leaned in, “You nasty little slut, you really want to get tag teamed?”
I nodded, but not taking his cock out of my mouth.
He gestured over to the side of the booth, and said, “Here's your chance.”
I looked over and I realized there was a glory hole in the booth. And there was a cock poking through it! Well, I wasn't going to miss this chance. I reached over and took this new cock in my hand, feeling it surge at my touch. I stroked it gently for a few minutes, then I started licking it while I stroked Brad with my other hand.
I wrapped my lips around and started getting the mystery cock wet, sliding my lips down slowly, dragging back up with my tongue, teasing his head. Then I wrapped my lips around and began a nice slow pace, getting into the feel of sucking through the hole. It was a little strange since I kept bumping my nose and face against the wall, but the excitement of being this anonymous cocksucker was taking away any of the awkwardness.
Once I got a nice pace going, Brad slipped in behind me and started fingering my ass. I kept moaning around the cock in my mouth and when Brad slid his dick into my ass again, I shuddered and moaned with the anonymous cock as deep in my mouth as I could take it.
Brad began matching his pace to fucking me, with how fast I was sucking. So, I kept speeding up and slowing down, enjoying the strange fullness at both ends. It felt so amazing, I couldn't really take it all in at the moment. I reached down to diddle myself a little, but the awkward position leaning against the wall while being fucked meant I needed one hand to hold myself up. I was able to get a little relief, but not much.
After several minutes, the scene on the film changed again, though I couldn't really see it, but I could hear lots of moaning and groaning, this got me really worked up, so I began sucking my random cock fast and steady, so Brad started plowing my asshole just as fast and even harder.
I was just about to reach down to play with myself when I heard a thump from the other side of the wall. I wasn't real sure what that was about, until I felt a gush of hot, salty cum shooting into my mouth. I guess that was my warning that he was about to cum. I figured it out pretty fast though, as he shot a really large load. I was about to swallow it, when Brad said, “Don't swallow yet, hold it in your slutty hole.”
Brad slowed down and pulled out, “Show me,” he ordered.
I obediently opened my mouth and showed him the flood of jizz that filled my mouth.
He patted me on the head, “Good girl. You want to swallow your treat?”
I nodded, and he told me, “Swallow it, slut.”
I gulped down the rather large, salty load when I heard something in the next booth. I realized someone was entering and putting money in their machine. I looked through the hole, but couldn't see much. The music and the distinctive sounds of grunting were soon coming through though.
“Is someone in there?” Brad asked quietly.
I nodded and said, “Yes, they just started a movie.”
“Good,” he smiled, “Put your fingers through the hole.”
I hesitated, but when he gestured, I reached up and put two fingers through the hole. Suddenly, I kinda wished I had some real gaudy rings and bracelets. Like a lot of bracelets, so they'd make noise when I moved and attract everyone's attention. Like I needed more excuses for people to look at me?
It didn't take much, since a moment after I put my finger in the glory hole, it was replaced by a pretty large black cock. At first, I was amazed it fit through the hole. I stopped gawking after a moment and began the same process. Starting slowly with my hand, then getting him wet with my tongue.
“Got a nice big black cock, I see, slut,” Brad said. “You ready for that?”
I nodded, “Fuck yes!”
Then I started wrapping my lips around it and using my tongue, getting this monster nice and wet. I worked on the large head for several minutes, but excited and a little nervous about taking in this beast. I then wondered what it would feel like in my ass, and shuddered briefly.
I think Brad took this as excitement, since he lined up as my ass again, teasing my hole with his cock head. I tried pushing back against him, but he pulled back, “Uh-uh, you get this in you, when you take all that cock,” he smiled wickedly.
I was annoyed, but also really turned on, so I turned my focus to pleasing the lover in my mouth. So, I got my lips and mouth nice and wet, and really worked on getting my partner nice and sloppy wet, first with my tongue, then sliding more and more of him into my mouth. Once I got about halfway down, he was clearly going to have to go into my throat to get any more, so I relaxed my mouth and throat as best as I could. After a few tries and some pretty heavy gagging, his giant cock head eventually popped into my throat. I squirted a little in my panties with excitement. Also, taking the rest was pretty easy at that point, I just had to slide down slowly until I felt my lips touch the wall.
At that moment, Brad made good on his promise and slid his cock into my ass, balls deep. Holy shit! I was completely filled with cock and I was loving it. So, I started working on getting a nice steady pace to please my mysterious partner while Brad worked on plowing my ass. Once I got a nice pace and was having this gorgeous cock go into my throat easily, I was able to really blow him well. Brad also found a nice pace and I was a happy little cock sleeve for both of them.
We couldn't have been going very long, and between the sounds of the videos and the frantic paces we were taking, I knew I was going to be flooded with cum and I was looking forward to it. I could feel my orgasm building, and I knew I wouldn't last much longer.
Just after that thought I heard the knock from the other side of the wall, and I pulled my oral lover back to just the head in and began stroking him quickly. It only took a few strokes and sucking on his head for him to erupt in my mouth. I thought I was being flooded there was so much cum. I was swallowing as fast I could but it still flooded out my mouth and down my chin.
“Oh yeah, swallow that load, my little slut!” Brad said, picking up his pace, and moments later he grabbed my hips, driving in deep and I could feel him pulsing in my ass, his cum flooding me. I was officially a cum dump. As I licked my black lover's cock clean, he slid back through the glory hole, and Brad slowed down as I milked his cock, I reached down and barely touched myself and I came with a shudder and loud moan. This was a pretty extended orgasm and I was milking Brad's cock while he slowed down and tried to catch his breath.
I leaned against the wall breathlessly, just reveling in the feeling of the moment. I was pretty embarrassed at how much of a wanton slut I'd become, but I was also really turned on by how much further I could go.
I returned to reality as Brad pulled out with a wet pop, some cum running down the crack of my ass, to pool in my panties. I was going to have another puddle filled pair of undies.
“Holy hell, that fucking amazing. You were on fire!” Brad sounded impressed.
“I was,” I realized, “I feel better now though.”
I pulled my panties up, trying to keep too much more cum from leaking out of my ass. I think I was going to be leaving a puddle no matter what.
“Damn! Well, if that's how fired up you get from going out dressed, I can't wait to see what you do when you wear some thigh high boots,” Brad grinned widely.
“Honey, you have no idea what I would be willing to do!” I laughed.
Brad just raised his eyes, and I was a little worried he might take me up on that challenge, then again, I was hoping he would.