Expliots of a Naughty Gurl

My sissy summer got off to a splendid start last weekend so much so I'm only now just getting a chance to share the juicy details. It started at the mall in Manchester a town where the chances of running into someone I knew or get recognized was slim. I managed to look pretty passable and seemed to blend flawlessly in public with maybe the pure exception of my shoes and the bag I used for a purse. I had posted here and a few other places about meeting up with a horny sissy for hot dirty hook ups.

In fact the first guy I met up with was from xhamster, he shall remain anonymous unless he wants to reveal himself. We had a deal where I'd make it worth his while if he bought me a box of condoms and some lube, and I hung around the food court while I waited for him to meet me there. He was nice even if it was obvious he was nervous, must of been in his 30's or possibly 40's. He claimed to have hooked up with sissies in the past but I'm not exactly sure if that was entirely true or not. Once we became comfortable with one another it was decided we'd begin our adventure.

We went to walmart together and I got two boxes of condoms [one flavored, one lubed] and some lube, he slipped money into the back pocket of my jeans. Sure enough the self checkout for whatever reason decided to not cooperate, and I was painfully nervous and embarrassed when the cashier came over to help us out. We paid and walked back to the car, thats when I noticed the humiliation of the visit had made me even hornier than I was before. I asked him to find somewhere secluded, and played with his cock in his pants while he drove.

By the time we found a secluded spot he was rock hard, especially when he saw that I had already opened a condom and was holding it in my lips. He wasn't too long but sorta thick, if I had to guess around 6 inches or so. I managed to get more than a little over half way before my gag reflex kicked in, so I slipped the rest on with my hands. I started sucking his cock like a hungry whore, like not only that it was my job but also my passion. I was a bit rusty, the last blowjob I gave being about 3-4 months ago.

He must of not only been really turned on, but extremely excited as well. Even with the condom on it must of only been like ten minutes or so before I got him off and made him cum. Like I said, I was sucking on him like a hungry whore. He finally spoke after surprisingly being silent for the whole thing, telling me that I did a pretty good job for a slut. I smiled and said thank you, I tied off the spent condom and slipped it into the zip pouch of my purse.

We thought about going back to the mall to fuck but decided against it, and struggled to find a spot that we could both agree on. I suppose this was a good thing as it killed some time so he could recharge. Finally I spotted the perfect place, a sleazy gas station in the rough part of town. It had bathrooms, which were accessible outside and didn't require a key so if they were locked it meant they were being used. I was hoping it had a mirror but sadly it didn't.

Nothing says a trashy tramp like fucking in a dirty bathroom I told him, unzipping his pants and freeing his cock. I quickly got him hard and once again put a condom on his cock with my lips, nearly getting the entire thing this time. I lubed him up generously and pulled down my jeans so I could pull my panties to the side and lube up my hole. I turned back to him and asked if he was ready to fuck my ass, reminding him that the only time he should stop is if I said the safe word "Red Light".

I quivered as he penetrated me, the feeling catching me by surprise. He started of slow and carefully, I loudly moaned when he buried himself balls deep. He asked me if I was okay and I moaned back in confirmation. "I'm ready for my anal assault" I said as seductively as I could sound, "fuck my ass hard I'm a bitch aching to be brutally butt fucked" sure thing he replied, damn your a filthy fucking whore.

He fucked me hard and fast, the sound of our bodies bucking against one another filled the nasty gas station bathroom. He pounded me balls deep which only made me moan more in pleasure. We went at it like this for quite a while, me bent over the sink with my jeans pulled down and my panties pulled aside getting my ass violated by a mans cock that I only just met earlier today. My plan of sucking him off so I could get a good fucking worked splendidly, I secretly tugged at my panty clad clitty managing to get off from this scene that turned me on so much more than I had imagined. I'm not sure if he noticed or not, he was in the zone fucking my ass like his life depended on it. Sense I was so sensitive after cumming, my moans and screams only grew louder spaced between involuntary twitches I was getting from the overly pleasurable fucking I was getting. He came pretty quick after all that, and once more I grabbed the condom to tie off and put in my purse.

We both were sorta stunned after all that as we came back to earth from our orgasmic bliss. Wanna go back to the mall I asked him, and he said sure I'll bring you back to the mall. I had sorta figured maybe we weren't done, but on the drive over there it became clear he was just dropping me off and leaving. I asked him if our hook up was worth the money he spent on condoms and lube, it sure was slut he told me. Before I got outta the car in front of the entrance we traded good byes and pleasantries. Its kinda hot that your gonna hang out at the mall after you just sucked and fucked me knowing that I got to you first.


I hung around the mall waiting for my next hook up. I started getting frustrated from flake outs, it seemed like a good hour or two I'd make plans only to have the guy never showed up. Finally I lined up a few blow and gos that worked out perfectly because it seemed like another had just arrived as I was finishing up with the previous one. I'd end up doing five in a row and they were mostly all the same, I'd stand out waiting for them by the entrance only to get in there car and suck them off once we found a private place to park.

The last one was one of the more difficult blowjobs I've ever given. His cock was massive it must of been 9 inches or so and pretty thick. He had claimed that he has never gotten off from a blowjob before, and made his objections to wearing a condom crystal clear. I told him if I couldn't get him off in an hour maybe we'll try something else. I struggled sucking his cock, slurping like a nasty slut nearly choking on it pretty often. It took me 53 minutes of this but I managed to succeed in getting him to cum from a blowjob.

It was starting to get late I had been out at the mall dressed up now for the whole afternoon and figured that soon I should start planning on going home and cleaning up. I edited my posts soliciting a last call hook up at the mall, and made another one looking for someone to host closer to home. To my surprise a couple saw my hosting ad and invited me to stop by, while someone who worked at the mall took the bait for my last call announcement.

The guy who worked at the mall had a slow store, and he was on break in the back room anyways. We went there got right down to the point of it all as we talked. He wasn't to thrilled about having to wear a condom for a blowjob, so I asked about anal which from his reaction was worth having to wear a condom for. He got a text and excused himself leaving me alone back there. He came back with another guy, one of his friends and asked me to explain everything again. I told them they could tag team me but had to wear protection, including for oral sex. His friend didn't object and mainly just wanted me to suck his dick while his boss boned me in the butt.

The guy whose dick I would be sucking sat in a chair that was low enough where I could be on my hands and knees. He had a smaller cock, slightly less than average but the perfect size for showing off my cock sucking skills where I could easily deep throat him. The one that was going to be fucking me in the ass was also average sized, but significantly thicker. I started sucking on the sitting guys cock while the man who was going to fuck me lubed up my hole and his own cock.

I wasn't as tight as when I started today, I could feel myself stretch around the cock violating my ass. He wasn't no time getting into a rhythm of pounding me hard enough that I could here his balls slap against me. It felt so good that it made me show off my cock sucking even more than I had planned, which only please the guy whose dick I was sucking even more. This was easily my first tag team in a year, probably two and maybe even three. It felt like it went by so fast, before I knew it I could feel the cock in my throat throb and pulsate as it came. To my surprise the guy giving me an anal assault stopped before he was going to cum, and pulled his condom off so he could squirt all over my face. mmm a facial was hot but I would of liked to know before hand. I snapped out of it when I heard clapping, one of their female workers had been watching for how long is beyond me. I quickly tried to eat the cum off my face and freshen up enough to make my way through the mall and back to my car.

It was an hour drive towards home but the detour I was making was to a couples house slightly nearby which was only about 45 minutes away. They lived in a slightly older development of houses that were modestly sized slightly towards the desolate side of that town.They were in their mid to late 30's and were having a date weekend off from family life. They invited me in and we chatted in their living room over wine. The wife thought she had some older clothes that would fit me if she could find them, but she wouldn't be able to look until after dinner to which I was more than welcome to have if I wanted too. I politely declined, but offered to finish cooking and serve them so she could look. I sarcastically said something about getting a make over in return for doing so, only to be delighted when she agreed to the idea.

I tried to stick to the servant role I was playing in stay in character but they were much to talkative to allow that for very long. I found out they had been married ten years, had two k**s, and tried to get a date weekend in every few months. They also agreed between them that crossdressers and transexuals technically weren't considered cheating on each other but they've only had the pleasure of entertaining them a handful of times so far. I also found out they had only just finished fucking a few moments before I had came over, and the wife told me the thought of eating her husbands cum out of her pussy turned her on much more than she had expected.

Once I had served them their dinner and they had started eating I sat at the table to keep talking to find out some more about what they wanted to do for our play date. The husband smiled and said anal, his wife confirming that part of the reason they invited me over is she didn't do that but her husband had really badly wanted to. He grinned and asked me to try and eat his wife's ass out if I could convince her to try it. I notice they seemed delighted when I told them I thought that would be a pretty hot scene. They asked me to tell them more about myself so I tried my best to give them the short and sweet summary.

I went to clean up the table and pick up the mess from dinner but they pleaded for me to stay and finish my story. I had gotten up to the point about today, and had left out the details except for saying that it was the first time spent as a sissy slut in a significant amount of time. They focused all their attention on listening to me give them a play by play of the days events which I described in deliberate detail emphasizing all the naughty juicy parts. I started cleaning up after I finished, and figured they went to freshen up or something.

The husband came down to the kitchen as I was setting the dishwasher nearly done with my clean up and shared with me that him and his wife were clean and had sorta intended to find someone who was DDF and wanted to be sure I wasn't stretching the truth about how all the slutty scene's I did today was done with protection for any penetrating contact. I proved to him I wasn't lying by showing him some of the tied up condoms I kept in my purse as souvenirs from my escapades. I also had a test results in my purse from 3 months ago with a sticker over my real name with the word Sissy written in place. He told me it was kinda hot hearing me talk about it, asking me about where in a relationship I need to be usually before I let my partners play bareback. Time and trust were the first things that came to mind, preferring to leave out the details about the few times I let guys skip the wait by buying me things or giving me favors while also not sharing how long its actually been sense I had a partner to consistently play with that I would let use me without protection. Before I went up stairs to start my make over I told him I'm game for whatever him and his wife wanna do.

I went upstairs to the master bedroom that had its private master bathroom. It was the kind of huge and spotless one you'd expect from a married suburban couple. She had pulled out two possible outfits for me and wanted me to pick the one I liked most so she can figure out what make up she would need to pull out for me. One was a well worn and nearly torn to threads see through lace baby doll with suspender straps that was black with a pink trim. The other was a never been opened but also purchased quite a long time ago shiny metallic black crotchless teddy that came with matching thigh highs and opera gloves. I opted for that outfit, but if I would of known the significance of the first one earlier I might of picked differently. She still had the boots she intended to wear with that teddy but we both knew they would never fit me.

I was to take a shower and freshen up while she got herself ready and prepared. It gave me a chance to do a once over on being all nice and smooth, at least it was significantly better than it was before my weekend adventures. I had noticed they left out an enema bag and nozzle on the counter, and figured I'd give it a go just to be sure I was all clean inside and out. Considering it all took much less time than either of us had likely expected it too, and soon enough I was drying off so I could start putting on my outfit.

The wife had came to check on me just as I was making sure the thigh highs and gloves were snug and fitting properly, surprised at how good I looked in something she bought herself but never got to use a decade ago. She figured sense I went with the metallic black, had dark hair and pale skin that a pseudo-goth style might be appropriate. She casually shared that she went through that phase when she was in high school, hoping it would all come back to here once she started. I would catch a glimpse here or a glimpse there, but she it pretty much under wraps while she worked.

She wasn't k**ding when she said she could give me a pretty good make over. Thanks to some of her help and skills I looked much more feminine than ever before, the only thing missing is figuring out what to do for breasts. My eyebrows were shaped, with the theme being a smokey sorta style contrasting with a sorta off white pale tone that was topped with bright red lipstick, fake eye lashes, and a braided ponytail for my hair. She snapped a few pictures, making me regret leaving my phone in the car. I made a mistake by trying to make a pose on her bed, that's when she told me their rule was the bedroom was reserved for just them.

She told me that we'll go downstairs, that they built a secret hook up room sorta when they finished their basement that was concealed enough that they didn't need to worry about people finding it that weren't suppose to like when they hosted big events at their house with family and friends. Her husband had been getting it ready and set up sense dinner was finished, so I followed her lead. Sure enough behind the washer and dryer was a sliding door that blended in well with the wall, behind which led to their little "dungeon." She was nervous about whatever or not I was kink friendly, and told me to just relax and let them know if I'm out of my comfort zone. Prior to k**s they had sorta went through some phases where they experimented with various kinks, and only recently started to get back into it again.

When I heard the word dungeon I had sorta picture maybe a much more hardcore BDSM layout to what was really there. The room was somewhat small, center on the far wall was a full size poster bed which had various beginner bondage tie restraints fastened to both ends. Hanging on the walls were a few floggers, a paddle, a riding crop, a ball gag, a ring gag, a few blindfolds, and a hood with only small eye holes and a somewhat bigger mouth hole. They seemed relieved that I was more interested in some of these things than they had initially thought I'd be. They asked me if I had a preferred position to start off in, off the top of my head I could think of two.

The first one would have me tied to the bed sorta spread eagle style but with my ass facing up. I figured this would be a somewhat easy position for the husband to have easy access to my rear, while also letting me sorta be face first in his wife's pussy. The second idea was similar sorta, except instead I'd be on my back with my legs in the air restrained to the poster bed. This way the wife could squat herself in a face sitting position, while her husband would be freely able to fuck me and they could even kiss each other while doing so. They rather liked my second suggestion, so we figured we'd start there. I got on the bed and sorta got myself into position while they stripped off their clothes. I was rather surprised seeing them both naked, they were both pretty smooth and good looking.

They took their time positioning me just right, before fastening the restraints to test it out. They told me to give it a few minutes to see if I could hold it without straining too much, they wanted me to be comfortable. They made out in front of me while we waited, clearly enjoying the mood we had set. I didn't really get a good look of her pussy before she smothered my face with it. I did get a good view of the husband's stiffening cock, it was a pretty good sized one without being too thick. Even though they last fucked hours before both were immensely turned on. Her pussy was soaking wet, and filled with cum. His cock fit perfectly inside me, snug but not too snug.

I could here them start kissing as they found the groove they needed to be in. The husband alternated between strong but slowly deep thrusts with a more aggressive faster shallow one. The wife rocked her hips back and forth enjoying the oral pleasure I was providing so much that her own orgasm caught her by surprise. This made them make out more, which only seemed to ignite a chain reaction of multiple orgasms in her that went one after another. The strain of all this was starting to make me feel sore, so when she went to get up and get off my face I asked if we could change positions. The husband looked towards his wife and without even him saying a word she confirmed his suspicion, she need a break to recuperate after all that. She'd still watch us, but we didn't have to pick a position with both of them in mind.

I asked the husband if he would mind laying down so I could ride him, which he was more than happy to do. At first we started where I was facing him, but the wife wanted a front row seat to our shenanigans. It was probably for the best because he kept slipping out of me the other way. I did my best to ride him hard like a hungry whore in the reverse cowgirl position, his wife egging us one and doing an amazing job making me feel sexy and pretty while her husband fucked me in the ass. I couldn't keep the pace I wanted in that position and needed to eventually request another change. I asked the husband if he had any favorites but of course he claimed to like them all.

I quizzed them if they had any handcuffs or restraints that didn't exactly tie you to the bed. The wife made a move towards a chest that was near here that contained a whole assortment of fun things, and I explained how one of my favorite positions is having my hands cuffed behind my back and bent over sorta like in doggy style. If we do it this way I don't want you to stop until you reach orgasm, I told the man standing beside me with the rock hard glistening cock. The wife found a pair of handcuffs, and happily put them on me and bent me over while guiding her husbands dick into my gaping asshole.

She must of really been enjoying the scene in front of her, I know I looked like a porn star thanks to her help. While she described the scene unfolding in front of her in elaborate filthy detail, I was reduced to mumbles and moans while her stallion of a husband merely grunted in between his precision like thrusts as he violated my now well used asshole. I think it was the dirty detail she was using to describe the sight of him violating a sissy's hole that sent him over the edge, I could feel him throb and pulsate as he filled me with cum.

Much to my delight his loads were larger than most people's, I surprised them with my request that I thought was pretty fucking hot. I asked him if it would be okay if his wife sucked the cum out of me and fed it back to me with a kiss, which they both quickly agreed was a sexy suggestion. My hole was slightly gaping, and it seemed like it was surprisingly easy for her to get most of it out. Otherwise her husband cumming huge was a significant understatement. She kissed me and fed it to me which I quickly swallowed while we continued to make out like two slutty girls. When we finally stopped her husband asked her if she thought about getting her ass eaten out.

He was surprised that not only did she agree to it, but seemed rather excited about it for once instead of usually avoiding the subject. He went to uncuff me, but I told him that I rather enjoyed it and would love to try and eat her ass with my hands cuffed. When it became clear that finding and getting into position would be challenging, I asked if instead he could help me get into a comfortable one. His idea was to sorta put me on my back and have her sit on my face, but it wasn't going to work with my hands cuffed like they were.

The position we ended up using was one where I was on my knees on the floor, she was bent over the bed and spreading her ass wide open. This was the perfect position for eating her out in such a way that it would be worth watching for her husband, who only managed to sit still and be entertained for a few minutes before grabbing a vibrator and trying to help his wife get off once more. Once he started talking dirty to her like she did to him earlier it didn't take her long to start getting off a few times in a row again. After the fourth or fifth she was spent and too sensitive to continue, but she was no a convert to the pleasurable feeling of getting her asshole eaten like a pussy.

Their attention quickly turned to me and how after all the fun play time we had this evening that I still didn't have a chance to actually cum yet. I did my best to sit up between them on the bed, and told them I was game for any idea they would have. They quickly asked me once more with emphasis on what way did I want to cum, sense it was only fair for the wonderful ones I had helped them have. I figured they had to be pretty spent by now as it was starting to get pretty late and they sounded like they had literally spent the whole day having sex. I told them well usually when I'm in sissy mode I'm in trouble if I cum without anything inside me. They seemed interested in the concept, and started talking about ways they could do it together.

The husband was pretty spent and not recharged enough to go for another round, which shot down the idea of her giving me a blowjob while her husband fucked my ass. I guess they had a strap on at one point but never fixed it, which squished reversing the roles too. That's when he had the idea that she should just suck my clitty anyway, and if I happen to cum without any anal play they'll just come up with a fitting punishment for it.

He moved a chair to the center of the room and changed the mood lighting that had been on into a more brighter setting so it'd be easier to see. They rearranged the cuffs sorta so it was like I was cuffed to the chair, and sorta talked between themselves about the scene that was going to unfold. She was to start sucking me and had to continue doing her best job possible for 20 minutes, and if by then I still hadn't cum it would be his turn to try except she would be eating my ass out while he did. It sounded splendid, but hindsight I think they knew how unlikely it was I would last that long.

She was a pretty skilled with her oral talents, I didn't stand a chance while she sucked my now rock hard clitty in front of her husband tied to a chair in their basement. It was evident that we were pretty tired sense between us there was little dialogue and even fewer noises except for the occasional slurp she did with my clitty in her mouth. Her deep throating and moaning while she did was too much to bear, and I squirmed in the chair repeating oh god oh god. She must knew I was really close because she stopped and managed to have just the head of it in her mouth as I exploded what was probably the most cum I've ever squirted in my entire life. It rivaled the creampie her husband gave me.

Without saying a word she sat on my lap and started making out with me feeding me back the load I just shot in her mouth. It continued for quite a while in my post orgasmic bliss, and her husband wasted no time telling us how hot that was. She was glad he liked it, but quickly turned to me and reminded me about the rules. I had been a bad naughty gurl and they were going to have to punish me. They each came up with an idea leaving me to pick one of them.

His idea was they'd chain me on my hands and knees gagged and take turns abusing my holes with dildos, doing so until I would cum again or one hour which ever happened first. While I was thrilled at the finish of that one, I didn't think I could do it without being really sore from the days prior events. The wife pointed out that this was a punishment, not round two. Her idea was they would at least gag me, but I could be restrained if needed while they each took turns spanking me with implements. The number of spankings itself not being important, just that for 16 minutes they'd do it as brutally hard as possible. The time limit being the exact time it took me to cum in the first place. I was expecting there to be more to the plan, and initially figured it would be easy being so simple like that. She laughed and called me a stupid slut in a joking manner, the catch was there would be no safe word or stopping it for those 16 minutes. I was at their mercy, which I should be as the submissive to their dominance it was there home after all.

I confided that there'd be no way I'd sit there and take it if it hurt badly enough, which is why she brought up the possibility of being restrained if needed. She fastened the ball gag in place while her husband set up the restraints on their home made "saw horse". I'd have my hands and wrists restrained in sort of an elevated position of being on my hands and knees. She asked me if this position was fine, and I told her yea its actually pretty comfortable. Then she paused and asked me if I was ready, I nodded in agreement while she smiled and said good. She fastened the ball gag in my mouth, while her husband said the punishment will begin in three minutes, they went to grab their favorite implements.

When the alarm goes off it marks the start of the 16 minute spanking I was going to get from the married couple I just hooked up with. I was gagged and bound to a saw horse not expecting the energy they would have for giving me the terrific spanking session I was about to get. They started much harder than I had expected, and I was now glad I was restrained for this. I struggled and squirmed from the hard painful impacts, screaming at the ones that really surprised me by how much they stung. To my surprise the one spanking me the hardest was the wife, with the husband merely playing along to her lead.

They spanked me so hard that it drew me to tears as I helplessly struggled against my bondage, my screams muffled by the ball gag but not silenced. It seemed like those 16 minutes took much longer that it should have, those last couple of minutes especially being pretty torturous. Finally the alarm went off which didn't stop my sore ass from stinging, but stopped the addition of new impacts. They took a picture and showed me the handy work they gave more poor abused bare bottom. Not only was it really red, there were welts and spots that were raw. They both agreed that was the hottest spanking they ever did. They didn't untie and gag me for quite a few more minutes, but once they did we went upstairs to unwind and start saying our goodbyes.

We both seemed pretty happy about the last minute hook up we all had, they wanted me to consider coming back again the next time they get a chance for a kink filled date weekend. I was pretty surprised that it was already well past midnight, I never in my wildest dreams would guessed a spontaneous hook up like this would turn out so pleasurable. They seemed pretty pleased too, confiding that inviting me over was sorta spontaneous and surprising for them too. We exchanged numbers and emails and promised to keep in touch. I got home much later than I had planned and expected, but much more satisfied too.