Surprised by Samantha

A little kink can go a long way. This is something I tell myself while waiting on a special package. A couple of months ago, a site I've been browsing posted a huge sale for ready to ship versions of their custom products.

Being able to hardly contain my excitement with little patience, I decided to do some yard work while awaiting the scheduled delivery. I was down on my hands and knees cleaning out the flower bed when from behind I heard "howdy, neighbor!" I nearly jumped out of my skin, as I was so deep in thought about my special night I had planned. She just giggled and said "calm down, scaredy-cat I won't bite ya."

I turned around to see Samantha my neighbor from a few doors down. She was out taking her afternoon walk. Samantha is gorgeous, standing at about five feet six inches, long red hair, blue eyes, and full breasts with thick hips and matching butt. To show it off, she was wearing a light pink tank top and blue jogging shorts. The kind of jogging shorts that rode a little high and let the cheeks peek through.

"It's about time you got around to spruce up the front yard. The weather has been warm enough for a few weeks now," she teased. "Heh, work has been really giving it to me lately. I'm just lucky I got the chance," I said rubbing the back of my head trying not to be too ashamed. Right then the courier pulled up with my special package interrupting out brief conversation.

"Ooh, whadya get? Something fun I hope," Samantha said playfully while raising an eyebrow. "Just some small electronics for a project," I blurted while trying not to blush. Samantha was still looking at the box when she made a funny face. Had she realized what it was? No. There was no way! The sender's address was a pseudonym meant to keep things private.

"Well, I should continue with my walk. Wouldn't want to keep you from all this hard yard work and your new toys," she said with a wink. There was no way I wasn't blushing now. "Ok, well it was nice talking to you, Samantha. Have a good walk," I managed to stammer out. Half turning around while still walking she called out "thanks! And if you want to swing by for a drink later, feel free. The weather this evening is supposed to be perfect."

I finished up outside and rushed back in. After taking nice hot shower, I decided it was time to check out my special delivery. Hastily ripping open the box, I made it to the surprise inside. It was a special order silicone squirting dildo from bad dragon. My heart fluttered with shameful excitement as I had never made such a purchase!

I had fantasized about fucking myself with a toy for some time now. When I found out that there were toys that could squirt, I couldn't resist. Even better was that it included a complimentary bottle of cum lube. Without hesitation I cracked open the bottle to see what made it special. The lube was stringy, viscous, and very very slick.

I was hard just examining my new naughty toys. The fake cock was about six inches in length and two inches in girth with a hefty knot just before the base. My bottom ached just thinking about it! "I'm not sure if I can't fit this into my tight little ass," I thought to myself. But I was damn sure gonna try.

Snapping me back to reality, I heard a quick tap at the front door. I couldn't answer it with this ridiculous erection, and needed a few moments to calm down. "Be right there," I shouted in hopes that whoever was there had the patience to wait.

When I got to the door I found a note that read "come on by for that drink. If you're still up for it that is. You can bring your new toys if you like. J/K -Sam"

I gulped so loud I'm sure the neighbors heard it. "Well, time to change and head to Samantha's, but tonight's special guest stay here," I thought aloud.

Samantha answered her door wearing a bikini top and boy shorts, her big perky tits nearly falling out of her top. She was grinning almost mischievously, and her hair was pulled back into a tight ponytail. I was in a polo shirt with khaki shorts and sandals. In other words, I was way overdressed. "Follow me, the drinks are on the back porch. I shoulda told ya we'd be hanging by the pool."

"That's ok," I replied. "I'm quite alright lounging on the deck with a drink. How was the rest of your walk?"

"Not bad. I ran a few errands afterward, and picked up the tequila for these margaritas. I hope you enjoy."

By this point I was already awkwardly downing my drink. Samantha and I had often exchanged hello's and hi's, but I never expected to be hanging out alone sharing drinks. I mean, she's so incredibly sexy and I'm the stereotypical geek that's somewhat awkward. But there I was, so I decided to do the sensible thing and get buzz going to let loose.

We chatted about standard neighborhood stuff. That was until about drink three or four. Or was it five? I couldn't remember, I was actually enjoying her company. That's when she dropped the bombshell, "so, are ya gonna tell me what's really in the box? Or am I gonna have to force it out of ya? I'm kinda bummed you didn't bring it," she exclaimed playfully and with a wink.

"I recognized the pseudonym. I have a couple myself. No need to be ashamed. They're quite intricate aren't they?"

"Umm...I'm not sure I..." "Oh, don't play dumb. I know you bought a toy from bad dragon," Samantha interjected.

By this point she was leaning over, cleavage on full display, wearing that devilish smile that she had been flashing ever since she saw the box. "It's a...a" "well, c'mon." "It's a squirting dildo," I managed to stutter out.

Samantha gasped, "that's so fucking hot! Please tell me it was for you?! Is this your first one? Have you ever tried anal before? What made you choose a squirter? What do you think of the cum lube? Exciting stuff isn't it?" She fired the questions off one after another almost without taking a breath.

"Well, I've had this fantasy for a while. And, it's just so embarrassing." "Oh, no. There's no judgment here. I love talking about these kind of things. I thought I was the only one until I saw your delivery. You always seemed so nice, I thought maybe I could broach the topic."

"I appreciate that. Um, well, you see I've always had this fascination for anal. Reading other's excitement about it online helped me build the courage to buy a toy to try it out. That's the one that was delivered today."

"Have you tried it yet?" Samantha asked, while trying to mellow her excitement. "No, not yet. I was going to try tonight actually. When you knocked I was about to go upstairs to prep," I replied.

"If you want someone to help walk you through it, I'd be happy to. Since you shared your fantasy, it's only fair that I tell you one of mine. I've always wanted to take someone's anal virginity. Would you let me be your first?"

How could I say no to this offer? My head was racing, my heart pounding, and well of course my erection was hard as a nail. "O-ok," I meagerly worked out. "Well, what are you waiting for? Go get ready, and be back in and hour with your new cock and cum. And don't be late, or you'll catch your first punishment too!"

I made it home with no time to spare. Bounding upstairs, I brought out the enema kit stashed in the bathroom to clean myself out. I made sure to fill the bag as much as I could, then slipped the slender tip into my puckered hole. A warm wave washed over me when I released the clip filling me up. I was in a hurry and luckily the bag was draining quickly.

I released into the toilet the first bag after struggling to hold it. Round two was just as enjoyable. The warm rush coupled with the sensation of being filled completely was almost euphoric. It was a shame being crunched for time, but I didn't want to keep Samantha waiting.

After a third bag I was clean and ready to go. So, I decided to check the time and see if I could fit in a shower. There was just enough time, but I felt like I was missing something. Ah! The starter plug I bought to train my ass. It was a small metal plug with a red jewel on the bottom (the only one available at the shop I visited last week). I lubed it up and slid it gently into my eager bottom with only a little resistance.

I quickly finished my shower and made my way back to Samantha's house with my small bag of goodies. She answered the door, but she wasn't wearing her bikini and shorts. Those had been swapped out for a lace black and red corset that hugged her curves and pushed up her breasts, making them appear even larger. Her panties were sheer black lace, and on her legs she wore tall stockings held in place with a garter. Needless to say, I was speechless!

"Get inside. NOW," she commanded sternly. "I told you an hour, but you're five minutes late. Don't you know it's very poor manners to keep a lady waiting?"

"I-I.."

"Shush. Now strip for me. I want to see what I get to play with." I began undressing in her living room. I felt slightly embarrassed to be so vulnerable, but also because I had kept Samantha waiting.

She walked around my naked body staring me up and down without saying a word. Then out of nowhere a firm slap landed across my right cheek and I let out a small whimper not expecting a spanking.

"Thank you for mostly obeying my requests. I know I didn't fully express my expectations, but you have done well. For the rest of the night you'll call me either Miss Samantha or Mistress. Also, now is your last chance to back out. So, if you're scared or uncertain, how's the time. I won't judge you. Is that ok with you?"

"Yes, Miss Samantha."

"Good. So, I take it you intend to stay and play along?" I nodded. "Excellent! I'm so happy you're willing to stay. For the rest of the night I'll be calling you by the names of slut, cum slut, and slave. That ass of yours belongs to me and will be referred to as your pussy. Is that clear?" "Y-yes, Miss Samantha. Thank you."

"Aww, what a polite little slut. Well, let's get you ready and dressed the part. Shall we? Get down on all fours and follow me."

I did as I was told when I heard Miss Samantha say, "oh, what a cute little plug for my pussy. I guess you wanted to be nice and ready for me. I do appreciate that, now come along."

Following Miss Samantha, I was led into a large room on the far side of her house. Looking around I saw various pieces of bondage furniture from a swing, a cross, and in the center on a pedestal there sat a padded bench with leather cuffs. The cuffs were situated on smaller padded arms that looked adjustable for the user's height.

Miss Samantha ordered me to stay while she walked across the room to walk in closet. I could hear her sliding hangers around and then open a drawer. She returned holding a small black leather collar with a metal ring on the front and another on the back. Miss Samantha was also holding a small push-up bra, light pink panties, and a short skirt.

"Sit up straight on your knees," she said almost sweetly. I did as was told, and the collar was placed around my neck leaving just a bit of slack. "This collar shows that you belong to me for the evening. Now stand up so we can try on the rest of your outfit. I bet you're gonna look so cute and sexy!"

Miss Samantha handed me my panties first which I slipped on. Next was my new skirt, and finally my bra. "You're starting to look the part my little slut," she cooed. "But there's something missing, something that says 'I'm a little cum loving cock slut!' Aha! Let's make you pretty! Come over here and have a seat." "Yes, Miss Samantha."

She sat me down on a stool next to a lighted makeup desk and began applying a modest amount of makeup. "Ok, now make a pouty face with those lips." I tried to do my best duckface impression I always say girls make. "That should do it. Just one last piece," she said. And then I found myself wearing a light brown wig staring at an almost unrecognizable person in the mirror. I was surprised to see I actually looked kinda pretty!

"Now, that we're done getting you dressed the part it's time for the fun to begin. Did you clean that little pussy of yours before coming to visit?" "Yes, Miss Samantha," I replied softly while nodding. "Good. Because if it isn't a nice clean pussy you'll receive further punishment. Your first punishment for being late was to get femmed up for me. I must say, I'm rather glad you took your time."

Miss Samantha walked seductively toward me with a leash in hand. Without breaking stride she clipped it to the front of my collar and tugged beckoning me to follow. "First things first. We need to brighten up that bottom to a nice shade of pink or red. Now, face away from me and place your arms and legs in line with the arms of the X." "Yes, Miss Samantha," I softly replied while doing as told.

I found that once strapped in, it wasn't the most uncomfortable position. But, it didn't offer much movement either. Miss Samantha lifted my skirt to reveal my bottom barely covered by the skimpy pink panties.

"This is going to sting, but I'll enjoy it!"

The first swats came from her hand. Slapping each cheek 7 or 8 times then rubbing them. "What a cute little ass! I can't wait to stuff that tight boy pussy of yours with a fake cock and fill it with cum. Ah, I'm so excited it's giving me chills just thinking about it! Don't worry, we're almost there. That little tush of yours just needs a little more color."

I couldn't tell what Miss Samantha walked off to grab, but I knew as soon as I heard it slap across her hand. She had a paddle. I gulped a nervous gulp and shivered with anticipation.

"Don't worry little slut. This won't hurt too badly." And then the first swing landed squarely across both cheeks. I whimpered as my knees went weak. "Oh, cmon. It isn't that bad. I've taken more than that. Besides, your only have four left."

The next four swats landed just as firmly. Not only did they sting, but they were landing across the plug in my pussy. The sensation reached my prostate and sent waves across my whole body. Ones I wouldn't soon forget.

"Ok, my little slut. That's enough. Time to get you over to the bench. Cmon."

"Yes, Mistress," I said with tears in the corners of my eyes.

Miss Samantha let me down, and led me across the room to the bench. She got me positioned and strapped down. It was actually quite comfortable with the padding and headrest. It did, however, leave me spread wide for easy access. "Do you like the little cutout? It makes it easy to reach that cock of yours. Well, tonight it's your clit, but the main focus is that pussy of yours. Let's see how your plug looks and if we can fit something more aptly sized in there. Hmm?"

She pulled my panties to the side to gently tug and coax the small plug from my hole with ease. "What a tiny plug. We'll need to do better than that. Did you even see the cock you brought me?" That's when I felt something warm and wet drizzle down my backside. "Warm lube is so much more pleasant wouldn't you agree?" "Yes, Miss Samantha. Thank you." "Oh, you're very welcome, sweetie. Thank you for being such a well behaved little slut."

I felt the new intruder pressing at my tight boy pussy. Miss Samantha continued to apply more and more pressure stretching me further and further. "Just relax and breathe easily. Your body will handle the rest." The pressure continued to build until I thought I might split in two. Then suddenly my tight hole gave way to the larger plug and swallowed it whole all except for the base. "That was so fucking hot. I need to see it again! Mmm...yes. Let's see that boy pussy gape, sweetie," Miss Samantha moaned as she slowly popped the plug in and out of me over and over.

"Are you sure your boy cherry hasn't been popped already? This pussy of yours is so eager to be filled. Do you like being filled, slut?" "Mmmhmmm," I slowly moaned. "Please, Miss Samantha. Fill me up. Ah. It feels sooo good mmmm." "No need to rush, slut," she said while repositioning my panties.

"Fuck you're so hot slut! I'm so fucking turned on right now. Let's see what else you can do!" And with that, Miss Samantha pushed the plug in deep and walked over to the toys laid out on the table. I couldn't see what she was doing, but it sounded like a bottle cap popped open.

Then she reappeared in front of me holding my bad dragon cock with the cum syringe full to the brim. "Open wide my little whore. I want to see how well you suck dragon cock!" I opened wide as she brought the tip of the dildo to my lips. Miss Samantha circled my mouth with the tip of the fake cock, and then gave a couple of slaps to either cheek. She was giggling with excitement, and I could clearly see the wet stain on her panties.

My mouth was soon filled with a silicone cock. "No teeth, slut. And be sure to treat it how you would like to be. I want to see enthusiasm and hear those sucking slurps expected from a slutty girl like you." "Ahhh hmmm," was all I could manage. That was good enough because Miss Samantha began working the cock in and out of my mouth as I made my best "O" face to suck on her cock. She began picking up speed grabbing a handful of my hair. The tip of the cock was now hitting the back of my throat causing me to gag. This response cause me to drool even more. It also brought Miss Samantha to test how deep I could throat this thick cock and how long I could hold it in the back of my throat. Turns out I was pretty good after a few firm pauses in the back of my throat. I was beginning to relax and the gagging was becoming lighter and more manageable.

"Ach...mmm...aghhh...ahhhh...ahhh...mmmmm," I continued as she pumped my face with her cock. But then she started to moan too. With each thrust I heard "ah ah ah mmm. I'm gonna cum. I'm gonna cum!" With the cock buried in the back of my throat, Mistress Samantha removed her hand from the back of my head and squeezed the cum syringe. "Aachh oorrrghh," I gagged as the fake cum coated the back of my throat and drizzled from the corner of my mouth. I looked up with tears in my eyes as Miss Samantha slowly withdrew her spent cock. Or so I thought. She still had plenty of fake jizz that she began spreading on my face. "What a good fucking slut. No, what a good fucking cum slut! You're officially a cum guzzling little whore now. Fuck that was hot! It looked like you enjoyed it as well. Did you like sucking my dick, cum slut?" "Oh yes, Miss Samantha! Thank you for cumming so hard. I loved having your cock in my mouth and taking load after load of your cum," I replied in my sexiest most enthusiastic voice.

"That makes me so happy that you would work so hard to please me. Now it's time to fill that tight little pussy of yours. I've got a little surprise for you as well. I've got the perfect harness for this cock, so I'll be able to fuck your brains out before filling you full."

"Please fuck my boy pussy, Miss Samantha! I can't wait to have your cock deep inside me. Please, I beg you!"

"Don't worry, sweetie. You'll be getting all my cock. Let's get those panties off, hmm?" As she pulled down my pink panties, my clit sprang free. "What is this," Miss Samantha asked. "Is that precum? Is my little cum slut getting wet? Well, I know what to do with that."

I felt two fingers swipe across the tip of my clit and then my panties being torn off with her other hand. "Open up and show me again how much you love cum," Miss Samantha demanded. I took her fingers into my mouth swirling my tongue around them to lick them clean. "Good work, slut." Then a small cock with a suction cup on the bottom was placed in front of me. "This is to keep you busy while I enjoy that pussy of yours. Be sure to give it plenty of attention!"

I began to please the fake cock in front of me while Miss Samantha got situated behind me. Again I was being opened up as she removed the large plug. I heard a quick "tchh" like a camera shutter after the plug was removed. "I'll just save this for later. Are you ready for my cock, cum slut?" "Mmhmm. Yesh, Missh Shamantha. Pleash fuck me and fill my pusshy wif your cock. Pleash," I managed to beg while trying to hold the other cock in my mouth.