Grabbing a bathrobe I move from the bedroom to the living room and to the door. As I open it, I’m apologizing that I was asleep in the other room. The guy with the cart was one I had seen behind the counter at check-in and passed once in the hall. He looked pretty much like a loaner that couldn’t get much better a job than ‘hotel gopher’. He didn’t look amused as he pushed the cart into the room, the door closing behind. He laid the ticket on the bar and as he moved the food to the dining table stated, “charge it to the room? Sign the ticket.” I added a nice tip and scribbled my new name, Lily Smith, across it without thinking. As he picked up the ticket, he looked at it and hesitated.
He asked, “What the hell is this, you can’t sign for Mr. Simons?”
LILY: “I’m a friend of his.”
BOB: “No, I was at check-in when he got here and he said he was alone. When will he be back?”
LILY: “I don’t know.”
BOB: “You’re his friend in his hotel room and you don’t know when he’ll be back. What kinda friend is that? And why didn’t you order more than one? What’s going on here?”
LILY: “Nothing’s going on, he stepped out for a while, I got a little hungry. He said he’d cover anything I needed.”
BOB: “No dice. If he kicks the tab back, I got to pay for it myself for my screw-up. You better cough up some cash.”
Now I started to panic as I had no cash. I guess he could sense my hesitation because he started to get a little harsh.
BOB: “Do you have some ID. Mr. Simons didn’t say anyone else would be here.”
Lily patting the robe: “Not on me.”
Bob not finding it humorous: “I’ll wait, go get it.”
LILY: “I mean I don’t have any here.”
BOB: “What the hell. You a hooker that snagged him?”
Lily a little pissed: “Hell no I’m not a hooker.”
BOB: “Well we’ve got a problem or should I say you got a problem. As I see it, not only are you trying to steal food but you’re trespassing. And if the cops see the ticket, maybe even credit card fraud. I think I need to give hotel security a call.”
LILY: “No, please. Don’t call security. It’s just a mix-up. What can I do to get you to let it slide? I promise Simons won’t make an issue of it.”
BOB: “I think I just need to get security in here. There’s no tellin’ what funny stuff you’re up to.”
LILY: “No please, anything. Just don’t get security involved.”
As he stepped in front of me, he got a wiry grin and said, “Anything? No security?”
Realizing he had bad intentions I replied: “Anything within reason!”
He sneered, “You said anything.,” and put his hands on my shoulders forcing me down to my knees. As I dropped down, the robe fell open and as he held it open he commented, “Yes, now that’s nice.”
Suddenly my mind wandered back to the statement Tatyana had made earlier. If he continued the path he was on, was I going to be able to get my head around performing orally?
His order quickly brought me back to the situation at hand, “Loosen my pants.”
With Tatyana’s warning ringing in my ears, I reached up, loosened his belt and unsnapped his pants. They immediately fell to his knees. His briefs were already starting to push out. As he stepped out of his pants he snorted, “Well it ain’t gonna climb out of my shorts on its own. Reach on in there and grab it.”
As I reached under his waistband and fished his semi-erect cock out, I was amazed at the heat it had. As I moved my hand up and down it, it grew very stiff. I kept stroking it hoping he would accidentally pop and the worst that happened would be me being sprayed with cum.
He squawked, “If I wanted a hand job, I could do it myself. Wrap your lips around it and start sucking. Take it into your mouth and use that tongue of yours. Use that pretty little mouth of yours and get it good and wet. Suck it like the pro I know you are.”
Obviously, he still thought I was a hooker. While I knew I didn’t want it in my mouth, I had little choice and leaned forward to let the tip in. His hand went to the back of my head and as he pushed me forward, several inches sank in. My natural reaction was to pull back and he popped out of my mouth. He snarled, “Suck it bitch or I’ll call security.”
LILY: “Okay, but you let me do it, no forcing it in.”
BOB: “Get busy, I don’t have all night.”
I closed my eyes and tried imagining how it looked for a girl to be giving head. It helped make the task a little more palatable but I was not sure what I would do if and when he squirted. I started to find a little rhythm as I rocked toward him and he started matching it rocking to me. I tolerated this for several minutes when he suddenly pulled out of my mouth. I thought ‘Oh damn, he’s gonna cum on me and all this work won’t count.’ My mind quickly turned and the thought ‘Oh man, I’m glad he’s not cumming in my mouth.”
He grabbed me by my arm, lifting me to my feet and push me toward the bedroom. As I stumble that direction, he pulls the robe off my shoulders leaving me in nothing but my panties. As we get to the bed, he turns me to face him and pushes me backward onto the bed with my legs draped over the edge. He lays down atop me as he starts groping one breast with his hand and slobbering on the other as he tries licking and sucking the nipple. This crude attempt at playing with my tits continues for several minutes as he alternates from the left to the right. The entire time his attention is on my tits, I can feel his cock pressed against my pussy separated only by the thin material of my panties. After his miserable attempt at arousing my breasts, he moved down my body. Grasping my panties, he strips them off me in a rough manner causing my legs to flail in the air. Dropping to his knees, he licks my pussy in a clumsy fashion, scarcely touching any of the sensitive areas. After a few licks, he shoves an index finger into my hole. I wince as none of his actions have begun to get me aroused and there is virtually no lubrication. After licking me once or twice more and pumping his finger into me, he said, “Better loosen up or my big ole cock is gonna split you in two.” My mind again began bouncing all over. It laughed at the thought that in his mind his less than average cock was ‘big’. I grimaced knowing that he would force it inside without any lubrication causing some pain. I was angered to think tolerating all this school-boyesque sex was for nothing beyond avoiding getting thrown out of the hotel. After a few seconds with my mind in turmoil, he stood. With one hand he raised my right leg by the ankle. Spitting into his free hand, he stroked his cock to wet it. If this was his attempt to apply lubrication, it was not worth his time. As he directed the head of his penis to my opening, he grabbed my other leg, raising it such that both were now up near his shoulders. As he pushed his cock inside, the lack of moisture was apparent as he only progressed a little before retreating and pushing more. It took four attempts before he finally sunk completely inside. He grumbled, “Damn bitch, loosen up a little. You’re gonna make me pop.” He continued thrusting hard into me and nature slowly started letting my pussy self-lubricate which made the action more bearable. While this was only the third time I was fucked after becoming a girl, I knew from a guy’s perspective, neither party could be enjoying this, unless the guy was depraved and rarely enjoyed sex with a woman. After a couple minutes more, he suddenly stepped back, pulling out and dropping my legs. The momentum caused me to slide off the bed onto the floor where I landed kneeling, but back on my haunches, staring directly at his erection. He stepped back toward me and growled, “Suck it some more.” I tentatively opened my mouth at the approaching head and again raised my hands to prevent him from shoving more than a few inches into my mouth. The taste of my stickiness on his member made it a little more palatable than before. Tatyana had nailed it. I didn’t want to be sucking a dick but it was now a necessary evil. I didn’t want to take a chance she was bluffing. As the distaste for the action raced through my head and within a minute of him putting his dick in my mouth, I felt a squirt of warm liquid from the tip. As he groaned, he reached down stroking the small section not in my mouth. A small dribble came out the tip but was of a minimal amount. Realizing he had cum, I hesitated regarding what to do. His cum was bitter and I didn’t want it in my mouth any longer than necessary so I closed my eyes and gulped it down. Pulling his rapidly deflating cock from my mouth he smiles down and said, “Yeah, swallow that sweet load of mine. Not every girl gets that chance.” I sat back on my haunches again watching as he started dressing. I had my hand pressed between my legs as the urge to pleasure myself grew after his lame attempt. I didn’t want to let him think he aroused me, rather it was Tatyana’s curse. As he tucks his shirt into his pants he comments, “So I guess you think you can stay in Mr. Simon’s room?” Fear suddenly seized me. Was he going to still call security after he got off? I had to think quick so I said, “I was hoping so. Maybe I can order some more room service, if you know what I mean.” He grinned, grabbed his crotch and said, “Yeah, I thought you might want some more of this. I’ll watch for your orders and deliver them myself.” As he walked out, he grabbed his copy of the ticket and said, “Don’t want to forget this, it’s gotta be paid. And remember when you order, Bob delivers a little extra.” As he walks out the door, I think, ‘yeah, it was pretty little.’
As soon as the door closed, I headed to the shower. I needed to wash him from my body. Fortunately, the shower included a hand-held shower massager. It was now later than I had anticipated so I blew off going anywhere that evening. I was able to get clean and get off with a well place-placed showerhead.
The next morning I awoke late. After accessing my situation, I was relieved that despite his boorish manners, the hotel jerk had checked one more goal from the list. I don’t know what I would have done if after all that work, he had blown his load across my tits or something. The two remaining goals posed differing challenges. I figured I would have no problem persuading a guy to have anal sex. The challenge would be persuading myself. Until Tatyana did her thing the other night on the table, I had never had a cock in my ass beyond being pegged by a girlfriend in a little role-reversal play. The other challenge would be to find a DOMME since I didn’t know how to recognize one from any other girl. The good news was that I was only two days into my six. Not wanting to chance another “room service” session, I headed out to get a bite. After thinking about the prior evening while sipping coffee, I decided I would be better prepared for my anal experience. I recalled passing an adult novelty store and video parlor several blocks away. I hoped to find some lubricant and maybe something to deaden my opening from the penetration. Strolling down to the shop I casually went in. I had been in several of these shops before but this was a first as a lone girl. The volume and variety of toys available always astonished me as I wondered who might buy some of them. Besides the two store clerks milling behind the counter, the only other person in the store was some older guy looking through the video racks. Ultimately, he worked his way to the door leading to the video arcade and tried to nonchalantly go in. I eventually made my way to the wall of lotions, gels, lubes and the such. It wasn’t far from the counter so I could now hear the two girls talking. They were both in their 20’s but one looked a little older than the other. The younger girl was bitching about her boyfriend’s work out of town and how she wasn’t getting any action.
The older quipped, “At least you’re getting some when he’s in town. I’m in the middle of a drought.”
The younger, “What’da mean, you’ve got your plaything, Tess.”
OLIVIA: “Naw, that bitch split. I guess she wanted a guy more.”
The younger: “I hadn’t heard. Shame ‘cause she was a fine looking piece of ass.”
OLIVIA: “Yeah she was fun. She even started reversing the roles and had learned well.”
The younger: “Ewww, I would love to have seen that. Hold on Johnnie is calling.”
As she stepped away from the counter to take the call, the older one walked my direction and asked, “Can I help you find something sweetie?”
LILY: “Oh, I’m just looking.”
OLIVIA: “Lubes or lotion? We’ve got plenty to choose from. Whatcha need it for?”
LILY: “Well, I kinda hoped to find something to make anal easier.”
Oliva sarcastically: “Ha. So your boyfriend finally talked you into some butt stuff and you don’t want to hurt your virgin ass?”
LILY: “Contrary to what you think, my ass isn’t virgin. In fact it got nailed earlier this week. I just want to be ready when it happens again, especially if the guy is as lame as last night’s hook-up.”
OLIVIA: “Pretty bad?”
LILY: “Terrible. But he thought he was a god.”
OLIVIA: “What you’re looking for are a desensitizing cream for your hole and a good lube for his stick.”
LILY: “Any recommendations?”
OLIVIA: “Well some of these are ok while others aren’t worth shit. Frankly, most of this is for those that just think they have to have something. I don’t buy any of it here.”
LILY: “What do you use and where do you get it, if I might ask?”
OLIVIA: “I have various ones but I order them from the net.”
LILY: “Oh, I guess I’ll have to make due cause I don’t have the time to order any.”
OLIVIA: “If you have a little time to kill, I get off in an hour and I’ll give you a couple sample jars from my stash at home.”
LILY: “Oh you don’t have to do that; I’ll just make due.”
OLIVIA: “Oh hell girl, you gotta protect that bootie. I don’t mind, I have plenty. Unless you’re in a hurry, go on across the street, get some coffee and I’ll come get you when I’m off. By the way, I’m Olivia.”
LILY: “Well if you don’t mind. I’ve got plenty of time. I’m Lily, nice to meet you.”
I spent the next hour savoring a steaming hot cup of chicory coffee before Olivia strolled in. I bought her a cup and my second as I invited her to sit down. We chatted at length about her job at the adult shop, how long she had been there, the kind of people that frequent it, etc. She admitted the clientele ran the gamut from perverts to couples looking to experiment to some real sex aficionados to horny people that used the video arcade to get off.
As we finished the coffee Olivia said, “C’mon lets go. We’ll swing by my place and see if there’s something that satisfies your ass. When you gonna let your boyfriend tag you?”
Not wanting her to know the plans and think I was just a sleaze: “I don’t have a specific timetable; just want to be ready when it happens.”
As we strolled several blocks away from the bars and shops, I found the French Quarter amazing. The narrow streets are lined with tiny houses that look to date back many decades. In the course of the chitchat conversation as we walked, I inadvertently reveal to Olivia that I didn’t have specific plans for the afternoon or evening and she admitted she didn’t have to be to work again until 2 the next morning. After several blocks Olivia led me up a set of concrete steps fronting one more of the old houses and unlocked the door. She motioned for me to enter ahead of her which I did. I took several steps in, blinking my eyes trying to adjust from the bright sunshine to the dim lighting and Olivia followed. I heard her drop her keys on the countertop and noticed she picked up something but was oblivious to what it was. As my eyes focused, I noticed a quaint little living room with a small dinette adjacent. Suddenly, I am bum-rushed against the wall a few steps ahead of me. As I am trying to make sense of what was happening, Olivia was rapidly encasing my wrists in a cloth binding. As quick as she had pushed me into the wall, she had my arms secured behind my back and was spinning me around to face her. Before I could say anything, she locked her mouth on mine and shoved her tongue into my mouth. Her tongue piercing that consisted of a little ball on a stud rapidly clicked against my teeth and brushed across my tongue as she probed around. My protests were muffled by her mouth over mine and with her weight holding me against the wall, I could offer little resistance and my arms were pinned behind me.
As Olivia broke from the kiss, I asked, “What the hell are you doing?”
Putting her forearm across my chest, she looked at me and said, “Oh come off it, surely you knew we would have sex after coming over here. You aren’t so naïve to think I would just invite you in, give you a few samples for your ass and send you on your way.”
LILY: “Hell if that’s what this is about, you can keep you shit and I’ll just leave.”
OLIVIA: “Oh no, that’s not gonna happen. You’re now my plaything and I’m gonna have some fun. You’re my sex toy and you’re gonna do what I tell you, when I tell you and how I tell you. You will address me as your mistress and only speak when given permission or asked. Any action contrary to this will be met with a punishment.”
As I struggled to free my wrists, “That’s bullshit. Let me go.”
Olivia pinching hard on my arm with her free hand: “I didn’t say you could speak. You’re not going anywhere until I’m thoroughly satisfied.”
LILY: “Oww! Shit that hurt.”
Olivia pinching me again: “Shut up bitch or the pain will get worse. Understand?”
Wincing at the pinch I mumbled “Okay!”
Olivia pinching me a third time: “That’s not how you address your mistress. Try again!”
LILY: “Yes, mistress, I understand.”
OLIVIA: “Much better. Now let’s see what we get to play with.”
With her arm still firmly in place holding me against the wall, she used her free hand to start unbuttoning my blouse. As it falls open with the release of the last button, she moved her hand up to cup my left titty and starts kneading it. After a couple minutes, my nipple was pronounced through the thin material of the bra. Olivia released her other arm taking the pressure off me. For a brief instant I thought about pushing her away and running but knew it would be futile as she would catch me before I could unlock the door. Her hands curved around my ribcage with the thumbs meeting in the middle. Sliding them upward while completely ignoring the front clasp on my bra, she forced the bra over my mounds exposing both breasts. I stood frozen as she squeezed them, brushing a finger across each nipple to excite them. Once the nipples were pointed, her mouth descended upon one whereupon she licked, sucked and bit it. After torturing one she moved to the other to repeat the process. She alternated several times causing my nipples to become sensitive. Stopping the titty-play, Olivia leaned back and her hand trailed down my stomach to my shorts. With skilled deftness her right hand popped the top button while her left pulled my face to her mouth and she resumed kissing me. As our tongues danced together, I could feel her slowly, almost teasingly, lowering my zipper. As the zipper reached the end of its journey, her right hand slid inside the shorts and around to cup my butt cheek. After a few squeezes of my ass, while still locked in a kiss, she pushed my shorts off the curvature of my ass so that gravity would take over and they would slide to my ankles. Her right hand moved to the thin strip of elastic comprising the top of my panties and with no trouble slid beneath it. The hand slowly snaked down following my ass crack toward my crotch. As her middle finger split my labia and pressed the opening of my vagina, I inhaled suddenly disrupting our kissing. Pulling my mouth back to hers, she pressed the tip of her finger slightly into the hole. As she retracted her hand and released me from the kiss, she smiled and said, “Hmmm. Seems my playground is a little wet.”
As she took a step back from me, I felt completely vulnerable. My blouse was open, my bra pushed above my titties, my shorts around my ankles and my hands tied behind my back.
Grabbing my right arm, Olivia starts to pull me toward the living room. It is all I can do to shuffle my feet and avoid tripping with my jeans tangling my ankles. As we take the few steps, she quips, “But it wasn’t about your pussy that brought you here, it was your ass.” As we reached the back of her couch, she forced me to bend over it with my waist resting on the top. Olivia quickly strips my panties down to my shorts and says, “Let me just have a little look-see as to what I’m dealing with.” As her hands spread my cheeks and she runs an index finger up and down, my hole jerks inward from the surprise. I hear her coo, “Mmmm, it looks like a nice tight rosebud.” I suddenly feel her warm breath in my crack and then the next thing I feel is her tongue flicking across the hole. As she swirls her tongue and forces it into my ass, one of her hands drifts down to my clit and starts rubbing it. This action causes the stirring in my crotch that must now be relieved so I relaxed my ass and spread my legs hoping she would continue her play. To improve her access, I stepped one leg out of the shorts and panties but relief was not in the cards. As Olivia stood, she smacked her hand across my bare ass, stinging it slightly and then grabs my arm to stand me up. As she pulls me, she orders me, “Lose your pants, you won’t need them where you’re going.” I kick my sandals, shorts and panties off as we walk into a hallway. Turning into a room on the left, I see a frame that looks a lot like workout equipment. There is a bench, a table, a couch, the metal frame, a small closet and dresser. Moving me to one side of the frame, she turns me to face her.
OLIVIA: “If you can’t remain quiet, I have several gags that will do the trick. Do you need one or will you behave?”
LILY: “I will behave.”
Olivia pinching a soft spot on my thigh: “I will behave what?”
LILY: “I will behave, mistress.”
OLIVIA: “Put your feet on those pads.”
Looking down I see a pad adjacent to each vertical post. I place my right foot in and have to spread a little to get my left onto the other pad. Olivia looped leather straps around each ankle and cinched them tight. Stepping behind me she starts loosening my bound hands while saying, “You will always have a couple appendages bound so don’t think I’m letting you loose.” Once my arms are freed, my blouse and bra are quickly removed. Grasping my left arm Olivia pulled it to the frame where she tied it. She repeated the process with my right. By now my pussy is begging for attention but I am unable to give it any. I try squeezing it but my legs are far enough apart that I can’t induce anything.
Stepping in front of me she smiles and said, “Now you’re completely mine. You’re my bitch and I’m gonna use you in ways you never imagined. Some will be pleasurable, some painful and some painfully pleasurable.”
Stepping to the dresser, Olivia opens a small jar and dabs her finger in the liquid as she returns to me. Beginning with my nipples, she rubs a small amount on each. After dabbing her fingers again, she reached down and smeared the liquid on my clit and the lips of my pussy. Putting the jar back she starts toward the door and says, “I’m going to get into my play clothes. You’re going to feel some warmth where I just touched, but don’t worry, it’s there to enhance our fun.”
After she left I began to notice a tingling in my nipples and a warming of the skin. As the tingle commences on my clit and labia, I am struggling to find a way to relieve aching in my pussy from the lack of attention. The sensations continue to grow more intense and my nipples are erect and pointed. Upon her return, Olivia passed in front of me and flicked each nipple with her finger. Both being super sensitive, I jumped. As she stepped to the dresser, I noticed she was wearing tight black bikini bottoms and a matching black bra. From behind she had a very nice ass. Extracting something small from one of the drawers, Olivia walks over. With her empty hand she plucks at my left nipple to bring it to a maximum point. It was really unnecessary as the gel she had administered was doing the job quite well. As she pulled the nipple outward, her other hand raised up and snapped a clamp onto it. The sudden pinch sent a shot of pain through the nipple into my tit. Letting go of the clamp, it drops pulling my nipple down painfully. She bounces the clamp with her finger causing it to rise and drop, repeatedly tugging the nipple. Not able to speak, I stifle a cry. Smiling she asks, “How does your new jewelry feel?”
I reply, “It is a little painful, but if the look pleases my mistress I will bear it.”
As she starts playing with my other nipple, it becomes as pointed and hard as the last. She again pulled the nipple out and snapped on a clamp. Laughing she said, “Funny thing about nipples, they will betray you every time with a little action. Now you will behave. Doing anything wrong will garner a tug on one or both of your nipples and those clamps won’t let go. Really misbehave and weight will be added.”
Olivia returned to the dresser and turning to me asked, “Would you like me to make you cum?”
Knowing the fire that was in my pussy from my inability to climax, I welcomed the thought. Hoping not to seem eager I replied. “Yes mistress, if my cumming pleases you, I would like that.”
Reaching into a lower drawer Olivia emerges with a vibrator wand that she paused to plug into a wall socket. The smooth round head looked to be about three inches across. While I had seen such toys in the shops I had been into, I had never seen one used. Stepping in front she raises the head into my crotch and starts the vibration on low. The head felt good against my sensitized clit and I wiggled trying to find the magic spot to get me off. As she pressed it into me, Olivia slowly ratcheted up the speed until it was vibrating vigorously. At that speed, I started to cum. The orgasm was just the relief I needed.
Smiling Olivia asked, “Did you like that?”
LILY: “Yes mistress, it felt good.”
Stepping close to me she whispered, “Good then let’s do it again.” And as she presses her mouth onto mine, she presses the vibrating head against my throbbing clit. It didn’t take long for my pussy to spasm again in pleasure. With her hand behind my head holding me in a kiss, I could only moan into her mouth. While she knew full well I had cum again, she did not relent holding the vibrator in place. My body was shaking and I could feel the cum leaking out and running down my legs. After what seemed like an eternity, Olivia simultaneously released my mouth and removed the wand. As she stepped back, my exhausted body went limp.
Olivia seeing the cum on my inner thighs said: “Eww, somebody has made a mess of themselves.” Running a pair of fingers up my leg, she scooped some of the goo and then pushed the fingers into my mouth to clean.
OLIVIA: “My goodness, where’s my head. You came here because you want to improve your butt-play. And here I am completely ignoring your butt. I know just what to do and it will make me wet at the same time.”
Spinning around the section of the frame in which I was bound, I was now facing inward with my butt outside. I hear her walk to the closet but am unable to see what she is getting. Walking back she says, “Your ass looks cold and pale, I have just the thing to warm it up.” With that a smack across one cheek with a paddle made me jump. Jumping again when the second strike landed, I not only felt the pain in my ass but also in my tits where the clamps would swing about when I jumped. The third pop landed on the other butt cheek but I was able to hold steady sparing further titty pain. Olivia was not new to this and knew immediately that I was anticipating the blows to minimize the clamps swinging. Taking her bare hand she passed it over the affected area and said, “Yes, now there’s some color and feel how warm they are getting.” Her gentle caress lured me into thinking she was done. Instead she proceeded to slap me with the paddle repeatedly in quick succession causing me to twist and jerk. After raining half dozen pops across my ass, Olivia stepped up close, pressing her body against mine and said, “Sometimes pleasure, sometimes pain. It makes me so wet when I spank the ass of my bitch.” Reaching around me with both hands, paddle hanging from her wrist, she cups both breasts and asks, “And how do the puppies feel?” I replied, “My mistress made them hurt a little while spanking me.”
OLIVIA: “Then I’ll give them a little rest. The clamps won’t hang down when you’re lying on your back.”
Freeing my hands from the frame she cuffs them behind me. While leaving the ankle bindings on me, Olivia releases them from the frame and leads me to the table and directs me to sit on it. Sitting with my legs draped over the end, she connects the bindings to the table. After uncuffing my hands, I am forced to lie down and my hands are tied to the other end of the table. Climbing onto the table, straddling me, Olivia looks down and says, “I hope you like pussy ‘cause you’re going to service your mistress now and my pussy is wet and horny.” Taking up a position such that she is straddling my mouth, she pulls her lips apart and I start licking her. She says, “Do a good job or I’ll have to punish you for failure. If I have to get the vibrator to make myself cum, you’re going to feel my wrath.”
I tongued her pussy vigorously and sucked the lips and her clitoris as best I could but nothing was working. I tried tongue-fucking her hole and while she remained wet, I could not bring her to an orgasm. After quite a while and with my mouth and jaw tiring, she sneered, “Looks like I’ll have to do things myself. If I get off this table, I’m gonna bring more things back with me than just a vibrator.” I increased my efforts to a frenzy but after a minute more she raised up. Without a word she dismounted from the table, went to where the wand was laid, picked up some things from a drawer and walked back. I could not see what extras she brought as she placed them on the table between my legs.
Resuming her position straddling my face, Olivia leaned back so as to expose her clit to the vibrator. She ordered, “Start licking and sucking my pussy while I show you how to get a girl off.” A few minutes of the sensation on her clit had her squirming on my face and as her cum started to run I lapped and sucked it up. After I cleaned up her first orgasm, she reversed her position. While her pussy was still over my mouth, her ass was now in my face. Looking back at me she said, “You can’t quite eat pussy right so we’ll see how well you eat ass. I want your tongue pleasing my bunghole until I cum again. Then you can lick me clean again.”
As she leaned back to avail herself to the vibrator again, her ass rotated so that her hole was directly above my mouth. I knew I was already in trouble so I was determined to do the best I could on her backdoor. As I licked and probed her with my tongue, I could hear the vibrator as it increased in speed. Within minutes Olivia is rolling her pussy back on my mouth and I am treated to another share of her cream.
She again dismounted but this time raised the head of the table so that I could see what was laid on it earlier. It looked like 4 colored clips. Stepping between my legs Olivia laid the wand next to me on the table. As she starts running her fingers up and down my pussy I get the feeling she is inspecting my flower. As she spread the lips apart, it was more as if she was focused on them than my clitoris or vaginal opening. I soon found out why.
Looking at me Olivia said, “You had one little job, make me cum by eating me. And you failed it miserably. I had to get a toy to do your job. Is that the way you treat your mistress?”
LILY: “No mistress, I am sorry. I am willing to try again if you like.”
OLIVIA: “Oh you will have another opportunity but I told you I was going to punish you if you failed. I think you take your pussy for advantage and therefore cannot administer pleasure to another. I’m going to make you very aware of your pussy.” Grasping one of my outer labia she attaches a clip. The pain of the clip pinching me was sharp and I bit my lip to avoid screaming out. As she attached a second on the other labia, I started to squirm a little.
OLIVIA: “So now you realize how sensitive a pussy can be. We’re just getting started.”
Returning to the first labia another clip was attached adjacent to the first. The final clip was placed opposite the third such that my pussy lips were pulled open by the weight of the clips folding out. It took everything I could to keep tears from flowing.
OLIVIA: “Yes, look at your hole completely exposed. Do my clips make you uncomfortable?”
LILY: “Yes mistress, my pussy lips hurt from them.”
OLIVIA: “Then let me see if I can’t relieve some of that pain.”
Sliding a finger down the valley created by the clips, she comes to my hole. Without hesitation, she forces her digit deep inside me. After a few pumps in and out a second finger is added. The fingering she is giving is doing the exact opposite of relieving my pain as the clips pull inward with every thrust into me hole. I try to shift into a position where there is less motion of the clips but there is nothing I can do. Finally she removed her fingers and picking up the wand she turned it on low and pressed it against my clit.
OLIVIA: “Have you ever seen your own cum oozing out of your pussy?”
LILY: “No mistress.”
OLIVIA: “That’s because you don’t respect your own pussy. You can’t give other pussy’s their due if you don’t worship your own. You’re going to get to see and taste it.”
As she adjusted the vibrator, I can feel the telltale signs of an orgasm building. As it peaks, it is a mix of pleasure and pain. The orgasm is wonderful but as my pussy contracts and spasms, the clips pull at the lips. As I reach my peak, I am looking down at my hole and see the cream develop at the entrance. Olivia sees it as well, and putting her tongue in licks it up.
OLIVIA: “Not bad but now you have to produce your share.”
Pressing the wand back into place, she immediately sets it on high. My ass is squirming as I rocket toward another orgasm. As my pussy emits more cum, Olivia is scooping it up with her fingers and delivers it to my mouth. Dipping her finger inside again, she pulls more out and I suck it from her finger.
As she pops the clips off my labia she says, “Maybe next time you get to eat some pussy, you will do it right and not just lick at it.”
LILY: “Yes mistress. I hope to prove my worthiness on you.”
OLIVIA: “Enough with oral sex, it’s time I get to fuck you. Ever been fucked by a girl?”
LILY: “No mistress. You will be the first.”
OLIVIA: “Excellent. Then both your pussy and ass are virgin territory. I think I have just the right cock for each. And I have a special one for you to start with.”
Transferring me to a short bench, I was on my knees, bent over with my ass and pussy exposed, hands secured to the post beneath it and my head just beyond the other end. Olivia secured my legs such that they were spread slightly. After she gathered a few toys, she positioned herself behind me. At first, she spreads my ass and her tongue is exploring my backdoor. Her tongue is replaced shortly later by her finger as she pushes it inside me. I flinch slightly as the only lubricant was her spit. As she pushes it in and out she explains, “I’m gonna use a little cream to desensitize your hole. I’ve got a special dildo that I love to use on myself as well as my bitches. It has a special surprise for your ass. When I’m done there, your pussy will be next.”
LILY: “Yes, mistress. I am your bitch for the taking.”
I feel her spreading something around my hole and inside the opening. I can feel a slight tingling begin. However, as soon as she removed her finger, I feel the tip of the dildo begin its penetration.
LILY: “Mistress, the cream isn’t working yet. You are hurting me.”
OLIVIA: “Shut up bitch. I didn’t say I would wait for it to work. I want you to feel every inch of this cock stretch you open. Feel every bit sliding in. Every ripple. Your ass will catch up in a couple minutes.”
After a couple changes in direction, the fake balls come to rest against my pussy and I feel the 7-plus inches of cock buried deep within me. Withdrawal is slow as is the reentry. Olivia is controlling the tempo with the intent of stretching my hole to its maximum before it is desensitized. As the numbness settles in and I become more accepting, she quickens the pace. The next several minutes are a variation of long, deep penetrations or fast, short stabs.
Shoving it in to the hilt, Olivia leans next to me and asks, “How long do you think a guy can last when fucking your tight ass?”
LILY: “I don’t know, mistress. Probably just a few minutes.”
OLIVIA: “What do you mean ‘you don’t know’. Didn’t you tell me you had just had anal a few days ago? How long did that take or were you lying to me to make yourself seem experienced.”
LILY: “No mistress, I wasn’t lying. It was just that I wasn’t paying attention to how long the cock was inside me before cumming. But it being my first, it seemed to stay in a long time as it shot off.”
OLIVIA: “Well maybe a couple more minutes and we’ll see how long it cums.”
As she resumed pumping the toy into my ass, she started rubbing my clit. I was confused by her comment but assumed she was talking about me cumming and was not about to ask. As the pressure on my clit increased as well as the thrusting of the dildo, I started pushing back to intensify the feeling. My ass was beginning to enjoy the pressure and that pressure was contributing to my approaching orgasm.
Seeing my action, Olivia commented, “Yes, there you go. I think you’re becoming an anal slut. Do you want to climax?”
LILY: “Yes mistress. Finish your anal attack on me. Make me cum for you.”
Suddenly I feel a warm discharge from the dildo. As it continues sliding in and out, the flow continues squirting into my ass. The feeling sends me over the edge and I start cumming on Olivia’s hand. She continues both rubbing my clit and pumping the squirting dildo into my butt. I can feel my bowels filling with the discharge and wondered if it would stop before overflowing. As Olivia pushed the dick in deep one last time, I sensed the flow from the toy had stopped but my pussy was still dripping its cream.
Olivia laughed, “So not only did you just get fucked by a fake cock, you got filled with a pint of fake cum. What your body doesn’t absorb will eventually leak out. But rather than it pouring out while I’m having fun with your pussy, I’ve got a little plug that should keep it in. Now squeeze your ass closed when I remove my toy until I get the plug in place.”
As I feel the dildo slowly extracted, I begin clinching my sphincter to prevent any loss. As the tip pops out, it’s all I can do to squeeze my hole closed to prevent leakage. It seems an agonizing long time before I feel the tip of the plug at my hole. Olivia slowly starts to push it in. I immediately realize the head is much bigger than the dildo but the desensitizing cream is now preventing much discomfort. Olivia is using the opportunity to tease my ass by inserting the plug to the maximum diameter but then withdrawing rather than inserting it completely. Once she does let it sink into my ass and my muscle contract around it, she starts to pull it back out. Finally, letting it stay, she taps it with her fingers saying, “That looks wonderful in your ass.”
I hear Olivia get up and move various things around, go to the closet to retrieve something and then to the dresser to do some unseen activity. I catch my breath, reflecting on the punishment my ass just endured and becoming apprehensive as to what lie in store for my vagina. Was she going to use a dildo on it? A vibrator? Was she going to fill it with fake cum? I was starting to get nervous when I sense her close behind me again.
As she taps on the butt plug again she comments, “That sure does look good in there. How I enjoy taking one in occasionally. But enough about your ass, it’s time to play in your honey pot. Here’s how it’s gonna go. I’m gonna fuck you in different positions until you cum. If I’m not tired, I might do it again. If I’m tired then you’re going to return the favor, only your positions will be limited.”
The next thing I feel is the head of a dildo spreading my pussy lips as she guides it toward my wet hole. After she has managed to push a couple inches in, she places her hands on my hips. When she pulls my hips back while pushing the dildo forward into me, I realized she has donned a strap-on dildo. At first she is kneeling behind me as she set a rhythm to her strokes. I’m enjoying the nice pace and figure with it I will be able to cum in a short time. This didn’t last for long. She then stands above me and is pushing down into my pussy. This is far less comfortable and not contributing to me climaxing. After a bit of this, I feel her reposition almost laying atop me while humping into my pussy. While the dildo was doing little to arouse me in this position, her midsection would hit the plug with every thrust and was sending pleasurable waves through me. Yet before I could get off, she stopped and withdrew the rubber dick. Walking to in front of me, I finally see the shiny, black dong that she was wearing. Kneeling in front of me she says, “Here suck on this while I loosen your hands.” Feeding a few inches into my mouth, I suck my own juice off the cock while she plays with the bindings. As she stood popping the toy from my lips, she said, “Slide back on the bench, I want to see if that’s far enough.” Scooting down the bench, the majority of my torso was off the bench. Having returned to my nether region, I noticed Olivia’s feet positioned on the floor parallel to the bench on each side. As I feel the tip of the dildo entering my vagina again, Olivia’s hands are now pushing my midsection down and my pussy is being met with upward thrusts. As we develop a pattern of me humping down and her thrusting up, it begins to arouse me quickly. When she tired, Olivia would sit still and push me down on the phallus. After several minutes, I start trembling as I climax. Olivia takes advantage of my excitement and begins thrusting into me relentlessly and I stay on the pleasure plateau for almost a full minute before she removes the toy.
Removing me from the bench, she leaves me kneeling with my hands bound in front of me. Because she has now bound my arms above the elbow, I am forced to squeeze my breasts between my upper arms. While normally this would not be painful, the nipple clips are intentionally caught under my arms forcing them to pull my nipples to the sides. As she stands before me, she does not need to say anything as I know what to do with the cum-covered dildo. Once it is cleaned, Olivia steps back and as she walks past, pushes me forward such that I catch myself on my arms and knees. The sudden pain of the clips pulling hard on my nipples reminds me that she has all the power and I am but a toy for her pleasure. A few agonizing minutes in this position are interrupted when she kneels next to my shoulders. She barks an order for me to open my mouth and as I do, she inserts a rubbery stub in and folds a strap around the sides of my face. As she pulls the new toy tight to my face, I look down the bridge of my nose to see the business end of a brown dildo sticking out from my face about six inches.
Positioning herself immediately in front of where I am propped on my arms, Olivia spreads her legs opening her wet pussy before my face. Seeing the cream that had amassed made me want to lick her every crevice.
OLIVIA: “Ever seen a pussy fucked up close?”
I could only shake my head no.
OLIVIA: “You will now. And you better fuck me good. I want to cum and then let you eat me out. I think you learned your lesson earlier that you need to do a good job on my pussy lest you will regret it more.”
Raising my head with her hand, she slid forward slightly so that the end was at her pussy. As I leaned into her, the dildo sank completely in and my nose bumped against her swollen clitoris. It took a minute but I developed a rocking motion that allowed me to pump the dildo into her. With each penetration, I was sure to rub her clit. As an extra measure, I would lean against her and wiggle the dildo while buried deep inside and strum her clit with the tip of my nose. It became obvious she was enjoying herself as she started rocking up to meet my thrusts. After a minute more, she grabs the back of my head, pushing it hard against her pussy and holding it tight. I was thrilled that she had orgasmed and was hoping to free myself of this toy and lap up her cum. That may have been my plan but not hers as Olivia extracted the dildo and pushed me in such a manner as to roll me onto my back. Having been on my knees with my ankles bound, I was forced now to be on my back with my knees up, legs spread, butt plug pressing on the floor, my arms squeezing my boobs and my hands at my crotch. Swinging a leg over she is now straddling my face, facing toward my pussy, and I see the dildo disappear inside her as her asshole is before my eyes.
As she moans in unison with the insertion, she says, “Time for my ride. And you get to see what your rosebud does when you orgasm. You may be tempted to play with yourself but if I catch you doing so, you will pay.”
Hoping to recapture her previous arousal I work to shove the dildo in rhythm with her twerking butt by raising my head. After a few minutes, she rises onto one knee, pulls the devise from around my head, and presses back down with her full pussy covering my mouth. I immediately start licking and sucking fervently and feel her pussy contract on my tongue. Her ass is pulled tight as all her muscles contract. I am gently rocking my lower jaw against the button of her clit to enhance the climax. As her orgasm subsides, I lick every drop from her hole. As she dismounts from my face, she smiles and says, “Much better my little pussy-eater, you pleased your mistress this time.” She leans down and kisses my cheeks, using her tongue to capture some of the cream that escaped beyond my reach.
After catching her breath, Olivia stands and goes about moving the table to align with the frame. Again I grow apprehensive of what further acts are to be performed. Even more than my apprehension, my excitement grows as I am now truly submitting to her desires and enjoying it. Even the pain endured by the clips and plug are now somewhat enjoyable. Unbinding my ankles, she moves me to the end of the table and directs me to sit on the table. Having loosened my arms, freeing them from squeezing my breasts, she directs me to lie down and extend my arms over my head. It is in that brief moment that I realize I am completely unbound and could escape. For some strange reason I do not hesitate doing as she has instructed rather than resisting. As she tightens my arms above my head, she steps to the side of the table.
Looking down at me she says, “You know you could have tried escaping just then, don’t you?”
LILY: “Yes mistress, I realized that opportunity was there.”
OLIVIA: “That was a small test and I was ready should you have tried. I am glad you didn’t fail as the punishment would have been severe. Instead, I will give you a small reward.”
Reaching down, she unclipped the nipple clip closest to her. My nipple felt strange without the pressure it had grown to accept. Leaning down she licks the nipple before sucking it into her mouth. The sensitivity of my areole was high and her tongue work had me squirming with delight. To calm my body, she put her hand between my legs and pressed gently on my pubic mound as if to tell me to calm down. After tonguing the nipple to a point and massaging my clit a little, Olivia moved to the other side of the table and repeated the process. By the time she concluded both nipples were tingling and pointed and she had started the desire building in my crotch again.
Olivia then moved to the end of the table and gently raised, first my right and then my left legs, attaching them to the frame above me such that I was almost folded at the waist. I was now spread before her on the edge of the table with the tip of the butt plug protruding from between my cheeks and my pussy building in need of relief. Again disappearing from my line of sight, she is doing something at the dresser.
Walking back to where my bum is she says, “We’ll find out if the desensitizing cream is still working by removing your plug. If not, we can add a little.”
As she grasps the end and starts extracting it, I can feel the hole being stretched wide. I don’t think I have ever been opened like that before today. Fortunately, the cream was still good as there was no discomfort. As insurance that I was not feeling anything, Olivia pushed it back in slowly and then removed it with equal pace.
Olivia looking down at my ass said, “Oh yes, you are gaping open just waiting to be fucked. I don’t want to disappoint you.” With that she began inserting the new dildo she had strapped on. It was larger than either the hand-held dildo she had used on my ass earlier or the one she wore when she fucked my pussy but it slid in with minimal resistance and my ass wrapped tightly around it. As she started her thrusting, she produced the wand again. I welcomed the possibility she was going to use it on me as my pussy was begging me for relief. Applying pressure to my clitoris, she continued long deep thrusts into my ass. I loved the pleasure she provided to both my pussy and my ass as I built toward an exhausting climax. After several minutes of varied thrusting and the vibrator on my clit, I started to clench up as the orgasm peaked. As she extended the pleasure I knew it was futile to try and wiggle away. She commented, “My goodness, your ass is squeezing the cock. I can barely move it in you.”
As she released the stimulation to my clit, I was able to relax my muscles a little where she slowly withdrew the dildo from my ass. Just for good measure, as my hole would draw closed as the tip exited, she would push it back in an inch or so. After her play showing her complete dominance of my ass, she stepped away from the table leaving me hanging and exposed.
I wasn’t sure what else might be in store for me since she had dominated every aspect of sex I could imagine but I was more than willing to participate at this point. I had literally become her toy so I spoke up without regard to potential punishment. In fact it may have been partly because I wanted her to continue.
LILY: “Mistress?”
OLIVIA: “Yes my little bitch?”
LILY: “I would like the opportunity to please you any way you wish without constraints. I love being your toy.”
OLIVIA: “Oh. So you want to satisfy your mistress and do whatever I ask?”
LILY: “Yes mistress. Please tell me what you want and I will do it.”
Stepping over to the table and loosening all the bindings Olivia says: “Very well, I want you to make love to me as if you were my boyfriend. You are to get me aroused orally and then fuck me until we both cum. But remember, a good boyfriend doesn’t cum before his girlfriend.”
I knew I could easily handle the oral portion but was perplexed as to how I might fuck her and cum with her. She stepped to the closet and pulled out an odd looking dildo. It was mainly L-shaped with a short end that curved to a bump. Beyond the bump was almost 10 inches of cock. Smiling Olivia announces “It’s a strapless. Before we start our love-making, I want to watch you slip it in nice and slow, working the pony end all the way inside you. Once you transform to a boy, you can approach me. I’m so horny right now that I want you bad.” After handing it to me, Olivia lays down on a mat on the floor. I position myself in a chair directly in front of her and decide I will use this opportunity to excite her and provide myself a little pleasure. I know I will trigger the need to get off but if all goes with plan, I will be doing that soon enough. I spread my legs wide so as to provide an unobstructed view. Staring into Olivia’s eyes, I take the stub pony end and start running my tongue around it eventually opening my mouth to accept it in. After a few moments of seductively sucking it, I slowly let it from my mouth and trace down my chest with it. As it reaches my navel, I reach down with my other hand and spread my pussy lips. As the stub passes over my clit, I let out a low moan and move it up and down. Olivia is focused on the end occasionally wetting her lips with her tongue. After teasing my clit a few times, I decide it is time to become her lover. Pointing the cock end upward, the pony comes to rest at my opening. Between the saliva I had deposited on it and my wetness, there was little resistance as it sank into me. Adjusting it slightly to better fit, I slowly started stroking the cock, bringing my legs closed. Olivia lays back and extends her hand beckoning me to join her on the mat.
Kneeling next to her we start kissing long and deep. I can feel her lust growing. I move my hands to fondle each of her breasts, bringing the nipples to points. Before moving my mouth to them, I gently rub each with the tip of the cock. When I leaned over to lick and suck them, I positioned to cock to press against her leg as a reminder of things to come. As I kissed my way down her tummy, she was already spreading her legs in anticipation of the oral pleasure I was to give. For a moment I seized a little control by lingering longer at her navel hoping to excite her a little more. When I gently brushed my fingers across her labia she shuddered slightly and with a heavy breath whispered, “Do it baby. Eat my pussy.” As I cross over her leg to assume my position between her legs, I make sure the cock slides down her thigh. Lowering my body I bring my mouth to her pussy. As I start probing it, there are telltale signs that she was already oozing cream. I took quite a bit of time licking and sucking every spot from her clit to her anus. If she started bucking against my tongue, I would slow it or divert to kissing her inner thighs. I was rewarded with several dribbles of her juice as I tended to her. Deciding it was time to advance things, I initiate some intense tongue and when she grabs the back of my head forcing me into her valley while pushing her hips upward, I know I am to be rewarded richly with a wonderful flow of her cum.
After she releases her grip, I start kissing my way back up her middle. Coming to her tits, I squeeze them together and turning my head back and forth kiss each nipple repeatedly. From there I raise up to position the cockhead at her pussy. I gently slide the tip up and down her crack, lingering at the entrance but not entering. Everything I did caused her to breathe deeper. Again in a heavy whisper Olivia says, “Don’t tease your mistress, give me that cock. Fill my pussy with every inch of it.”
Leaning forward slightly, I slowly sink it into her until I come to rest against her. I lay down on her and slowly start withdrawing and penetrating her. She raises her hips to meet my thrusts. I am doing it very controlled and tender almost as if truly making love. As she wraps her arms around me, we kiss deeply. By now the pony end has started pleasing my lust-hungry pussy and I am instinctively increasing the pace. Before much longer, Olivia is pushing up to receive my thrusts and we are humping in unison quite vigorously. I call out, “Cum for me baby. Let it go and cum.” My chorus is met with a responses of “Yes, give it to me baby. Cum for me, love. Yes that’s what I want. Fuck me harder.” As Olivia arches her back in ecstasy I am pushing against her to invoke my own orgasm. We are both shaking as neither wish to stop the action. Drained, I collapse onto her heaving chest and kiss her deeply. I roll off and lay next to her, both basking in the euphoric afterglow. I whisper, “If it’s this good, I could be your little bitch forever.”
After we catch our breath, Olivia asks, “Did I hurt you too much?”
LILY: “Oh no, it proved to be a pleasurable pain, like you promised.”
OLIVIA: “I am glad. I get so turned on by making people submit to my sexual whims. And you did so well.”
LILY: “Do you like dominating only girls or do you do anybody?”
OLIVIA: “I prefer girls because they can have so many orgasms, big or small. But there are a couple type guys that I will train.”
LILY: “What type are those?”
OLIVIA: “There’s those that think they are sex gods but in reality, aren’t worth a shit in bed. I usually turn them into sniveling lumps.”
M thinking of Bob at the hotel: “Yeah, I’ve run into one of those recently. And the other?”
OLIVIA: “Mainly guys that just aren’t really sure of themselves. I pick up the majority of my subs out of visitors at the boutique. They come into the shop and mill around marveling at the toys or the various video genres but don’t know what they are looking for. I can usually get a sense if I talk to them about something. Sometimes, they get nervous and bolt but if I get them talking, I might steer them one direction or another to test their willingness to be unconventional. Sometimes to set my hook in them, I’ll slip into a video booth with them that is showing what we had been talking about. Once there I might let them cop a feel of my wetness, give them a little stroking or maybe a brief oral sample. After that the majority will follow me anywhere.”
LILY: “How do you pick the girls?”
OLIVIA: “That’s easier. Most girls secretly want to experience another woman. Like you today, I think you knew coming to my place was likely to result in sex. You just didn’t know I was going to dominate you. It doesn’t matter whether the girl is straight, bi- or lez, they seem willing to come here. Once here, the rest is simply training her to the better way.”
LILY: “Are there any that refuse to submit?”
OLIVIA: “Yes, but rarely. I just let them go their way. But by the time we are finished, they are sexually exhausted.”
LILY: “I liked you sexually exhausting me.”
OLIVIA: “We could play this way frequently if you want. There are so many more things I would love to do with you. You could be here as often as you want.”
LILY: “But what about when you bring others home?”
OLIVIA: “That would just add to the fun. I can teach you how to be a Domme or as my sub I would make you do things to the other sub.”
LILY: “Mmmm, I’m getting wet just thinking about it.”
OLIVIA: “Too bad. You’ll have to wait. Your mistress needs to get some rest before I go to work.”
LILY: “What time is it?”
OLIVIA: “Almost 11. We can catch a couple hours before we leave. Come curl up with your mistress and let me hold you.”
We slept until 1:30 when she woke me to go. Kissing me deeply as we get to the front door Olivia says, “I hope to see you some more. You know where to find me.”
LILY: “I have a couple people to meet over the next couple days but I’m open after that.”
Olivia handing me a small bag: “Oh that reminds me, here are the items you came for, if you pardon the pun.”
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