Boss Me Please

by Amy Brent

  “I was thinking the same thing and I do believe that I’m going to give you a bonus. It’s a basic starter kit, but it will help you to enhance this evening, until the windows are steaming up.” She presented me with this odd assortment of items including a curved vibrator with multiple functions, along with a very discreet blindfold and fur lined handcuffs. She slipped it into a nondescript bag with no discernible markings to say where it came from.

  “I’m not sure if I’m going to use any of that, but it’s nice to know I’ll have it at hand.” I did enjoy pushing the envelope with my own pleasure, but could I even dare do something like that in the bedroom with someone else. The box Anthony had in his closet was not for the faint of heart. He was a kinky little son of a bitch, but it was his charm. It was just one of the reasons why I had fallen for him. He didn’t have possession of that box tonight, so maybe this would make a perfect substitute for what was missing.

  “If I were you, I would tell the guy you’re with that he shouldn’t be insecure about his body or his performance. This has nothing to do with that and is only an aid to turn things up a notch. I get this feeling from the look in your eye that you’ve already become quite aware of his obvious desires. Maybe tonight, you should let him play director.” She winked at me encouragingly, as I walked out of that sex shop feeling a little bit better about myself.

  I remembered what I looked like with a particular item on and I had no reason not to believe Bailey would be putty in my hand. I was even thinking about using the handcuffs and the blindfold to really give him something to remember. I’d already sent him a text message to tell him what room we were staying in.

  Thankfully, the shops were pretty much in walking distance of the hotel. I was able to do some necessary window shopping and peruse some of those finer things in life that only money could buy. I was not much for material things, but Anthony was going to have more than enough. I would never take advantage of him in that way, but I would not deny him the opportunity to shower me with gifts.

  I took a long walk in a nearby park sitting by a stream and feeding the ducks with that package of naughty things not too far away. Anytime somebody got close, I would grab that package protectively and hang onto it for dear life. I didn’t want the unnecessary possibility of someone knocking it over and seeing my dirty little secret.

  I got a text message back “I’m going to be a little late to the party, but if you want to start without me, then by all means. I think tonight is something to celebrate. I’ll know more information in an hour or so, but I am optimistic that things are going to work out. There are a few contentions that have to be ironed out, but it doesn’t look like they are unwilling to bend on a few key issues. My coach is doing most of the negotiation, but he’s using my notes to get me what I want.” I was happy for him and it looked like things were looking up.

  I had paid cash for the hotel avoiding any kind of entanglement of the credit card getting flagged or for some reason the credit card company informing my parents that I had used it for more than just an emergency. My father would not be very happy with me and I’m sure Allison would have a few choice words that were a little colorful.

  I found my way back to my room by avoiding the main lobby or any of the staff. It didn’t seem likely any of them would know me, but I wasn’t about to take that chance. Being pregnant was one thing, but having it splashed across the front page of the local newspaper was not something that I was looking forward to.

  I called down to room service and got what they call a surf and turf dinner. I ordered it before hand, but I told them that I would not need it, until the second part of my party arrived. They were quite accommodating. This hotel was not exactly four stars, but it was as close as I was going to get in this town.

  I laid the items on the bed and looked at them with the eye of a man. I actually found myself grabbing my crotch like a man would if they were feeling the least bit excited. I took off the trench coat and laid it very carefully over the chair. I took off my white crisp blouse. I undid one button at a time and then slid it over my shoulders and down onto the floor at my feet. With each item of clothing, I made a trail from the door to the bed with a smattering of rose petals to give it that extra touch.

  I was in my birthday suit. Looking in the mirror, I had to admit that I looked pretty damn good. I would’ve made the perfect plus size model. I had thought about it, but there was always something pulling me back from taking that kind of insane risk.

  It was a couple of hours later and heading into the 9:00 hour. I just received a text that he was on his way and would be here in less than an hour. He didn’t say anything more and I wasn’t going to ask any questions in case it was supposed to be some big surprise.

  I put on the very revealing item, staring at myself from every angle, before lying down on the bed. I’d already made the bed with the silk sheets and the candles were ready to be lit. A box of matches laid on the night stand with the prerequisite alarm clock that was provided by the hotel. I fiddled with the dials, until I found a station of easy listening that was perfect for the kind of mood I was looking for.

  “Your father is going to be here any second.” I was surprised that I was even talking to the child like it was already out of the womb. I’d heard that it was good to let the child know who his parents were before he came into the world.

  I called down to room service to send up the meal, but I changed my mind at the last second. I instead went with the staple of strawberries and whipped cream. I was sure that we would be famished after we were done and maybe then we would need something more of protein to keep our energies up. I was a little apprehensive and anxious at the same time. Our first time together was by my hand and this time I was going to let him take control of the scene.

  I heard the clanging of wheels and I had requested they just leave it and go. I was really in no condition to open the door without making some bellboys night. I slipped the blindfold over my eyes and I was essentially vulnerable and exposed in a way that I had never been before. I slipped them over my wrist and I was now ready to greet him with a sight he would never forget.

  Chapter nine

  It was not more than 10 minutes later that I heard the door opening. “I’m guessing that this tray was left outside for…” He stopped and I could hear him still standing there, but his words had got caught in his throat. “I knew we had something to celebrate, but I didn’t think it was this special. Don’t get me wrong, I love seeing you like this.

  The sight that greeted him was of a voluptuous young woman with her hair fanned out across the pillow and wearing a red black widow kind of outfit with the garters and stockings to complement the outfit. The cups of the bustier could barely contain me.

  “I thought you deserved to have the tables turned. I was the one that took advantage of you and why shouldn’t I reciprocate in kind. I’m pretty much a captive audience like you were the other night. I’m sure that I’m asking for it, but I’m pretty much right here for the taking.” His hand touched my face and moved down between my perfumed breasts. He lingered there a moment, before pulling down the cups, until I could feel the cool breeze wafting over my nipples.

  “I’m so glad that you are willing to put yourself in my hands. I never thought for a moment that you would be this kind of girl, but I’m pleasantly surprised. It’s one thing to go out of your comfort zone when you know the guy can’t do anything about it, but it’s another altogether when both partners are very much in the moment.” I hadn’t asked him about his meeting. It could wait for the time being.

  He lifted my wrists and the jangle of the chain from the handcuffs affixed around my hands was thrown back behind my head. He got on the bed and straddled me, until I could hear the unzipping of his pants. I felt something hot against my lips and I gave it a lingering kiss with my lipstick now marking my territory.

  “It doesn’t look like you are very comfortable, but I’m grateful for the effort.” He was pushing insistently against
my lips and I opened them with no particular fanfare. He slipped in and it was a reminder of what I had done the other night. This time, he had a grip of my hair and was pulling me towards him while shifting his hips enough that he was force feeding me his junk.

  I gagged for a moment, but teaching myself the finer arts of deepthroating had done wonders for my self esteem. I heard his moan, as he felt the constricting walls of my throat closing in on him. Thankfully, there was a pillow underneath my neck. It made for the perfect angle to fuck my face. He was igniting those nerve endings and causing me to squirm with his hand now reaching to stimulate another part of my body.

  “I’m gathering you did this to me the other night when I was totally shit faced. I regret that I was only there in spirit, but I am here now. I’m going to make the most out of this. Your lips are a scorching heat and your tongue seems to have a mind of its own.” I had wrapped it around him several times and was pushing him to his limit and beyond.

  He took his soaking hot cock out of my mouth and placed it between my breasts. He used two hands to fold the hefty meat around his Johnson. He used what I had given him with my mouth to supply him with the necessary sensation to slide back and forth between my tits. When he emerged, I would lick the head and give it that little bit extra. It was the most sensitive part on a man and that was no more obvious than how he was becoming quite the animal in the sack.

  With no warning, he stabbed it back into my mouth. I couldn’t see him, but the obvious sound of the headboard slamming up against the wall was a byproduct of his two hands holding onto it for support. “I’m going to fucking cum and this time I am going to be here for it. You know that it’s coming and you can feel it… YESSSSS.” His knob expanded and then his whole cock pulsed with a life of its own. There was a continuous flood of one shot after the other. It filled my mouth. I was worried that I wasn’t going to be able to take it, but I even surprised myself.

  He flipped the blindfold up and out of the way. It took a moment for me to adjust to the flickering candles and the man with his two knees on either side of me. It was kind of ironic to think that I was in this position on top of him the other night and now here he was doing the same.

  “I wasn’t given the chance to do this the other night.” He followed those words up with licking my nipples and making this sound of enjoyment from tasting the strawberry gloss. It was the same that I had worn the other night, but I’d forgotten that he would be in no condition to sample the wares. “Fucking delicious.” He jumped off of me, stripping up his pants and showing me his hard packed cheeks in only the flicker of the candlelight. He came back with the strawberries and whipped cream and began to spread it over my lips, across my nipples and then trailed those berries down to my most treasured of areas.

  He stared at me the entire time that he was eating those strawberries off my body, until he was pushing my knees apart and opening me up to a more crucial and determined exploration. His fingers pried me open and then I watched, as he circled my clit with the whipped cream and then sucked it off with me practically flying to the ceiling.

  “Fuck… I have been missing out on all this. I was so presumptuous to take what I wanted… the other night.” I could’ve easily put my hands down on top of his head and wrapped those handcuffs around his neck to make sure that he didn’t go anywhere. I didn’t do that, because he was perfectly happy to satisfy his need to taste me. “You’re definitely not one that is easily shocked. Yes…get that fucking tongue in there where it’s going to do the most good.” I could tell from his technique women of any age would be putty in his hand. If only he knew this could be his secret weapon.

  He stared at me from below with his tongue moving at a remarkable pace. He had my body practically jumping off the mattress. He tried to hold me down, but it was like trying to stop a hurricane from blowing through town. I bucked and thrashed under his enthusiasm to get me off. I came with my teeth digging into my tongue. That didn’t prevent anything and the animal sounds coming from my mouth was most likely giving a lot of the patrons in this place something to think about. Hopefully, my performance would convince them all to jump their significant others and join me in a cacophony of sexual sounds echoing down the hallway.

  Anthony lifted me to his mouth and inserted his tongue repeatedly with a very agile instrument of sexual torture and desire. He produced the curvature of that dildo. The package of goodies was coming in handy. He turned it to a very high setting and it began to vibrate. He smiled and stuffed the length of it inside me. I came up on my elbows with my mouth wide open and nothing coming out.

  “AHHHHHHHHHH.” I howled with delight, as he slid that plastic appendage back and fourth against my convulsing walls. My juices were squirting down the length of it. I’d never felt anything quite like that. I lost my cognitive abilities to say anything at all. The only thing coming out of my mouth was my craving for him. It was all caused by him taking the reins.

  I had no idea how long it lasted, but it felt like he was trying to pull me apart piece by piece. My mind was a jumble of images and soon he was lifting my ample legs onto his shoulders. He pressed into the crevice between my legs and soon found how greedy my little pussy was. It pulled him in on a wave of liquid fire that had his mouth parting. He kissed me with a fever pitch, slamming into my body with the bed groaning in response.

  “I knew this was going to be something, but I never imagined you would far surpass my expectations. Your pussy is fucking tight and it’s a little surprising considering your size. I’m certainly not complaining, but I wasn’t ready for this.” That was seen in his eyes and the way that his face had flushed from the exertion of my little hole clamping down on him.

  “I know you’ll always be by my side, Anthony. Tonight is for lovers and for the type of sex that will always have you coming back for more. Fuck me and don’t treat me like some frail flower that’s going to break. I can take a lot more and I will always be able to measure up to you in one way or another.” He was really pounding the living daylights out of me. My eyes were sliding up into the back of my head and then I was gyrating with such a force that it felt like a bomb going off inside me.

  “Oh yeah…ride that orgasm… Jessica.” He was doing his best to contain himself, but the feeling of me going off like that couldn’t have been easy. I was amazed that he was able to hold strong and even managed to turn me over on my hands and knees. In this position, I was essentially giving him a bird’s eye view of my overdeveloped posterior. He plugged me solidly. This position was uniquely made to get that maximum penetration and depth.

  “Slap my ass…pull my fucking hair…treat me like a dirty little slut.” The resounding crack jiggled my ass and made me moan into the pillow at my head. He pulled my hair back and the pain of wrenching at the follicles had definite advantages. I was beside myself. Soon my legs and my arms gave out. I was flat on my stomach and he was still power driving over top of me with his two hands touching the pillow on either side of my head.

  “I’m on fire for you, Jessica. Cum with me and let us take this journey together…cum with me…ride the fuck… NOWWWWWWW.” He gave one final lunge burying himself and then letting go with the same kind of intensity that I’d felt the other night. He continued to fuck me through his orgasm and I rippled along his length. I pulled out of him every little bit that he could give me. He finally pulled out slowly letting me feel every inch then dropping back onto the bed right beside me.

  “That was…repeat after me…fucking amazing, Anthony.” This was a bond that could not be broken and I had the recipe for love. It was right here in front of me.

  “I didn’t even tell you that I signed the contract. It was a long and arduous process, but I’m glad it’s finally over. I take off for training camp in a few weeks and I want you to be there. I’ve already lined up a few real estate agents. Together, we will find our little love nest away from those that would consider what we’re doing taboo. After I finish the season, I want to approach your father and
my mother.” He could’ve asked me for anything at that moment and I would’ve gladly given him it.

  “I could die right now and be a happy woman. I don’t know about you, but I’m famished. I know for a fact that they have this surf and turf dinner for two on special. Why don’t you give them a call? I’m a little tied up at the moment.” I raised my hands with the handcuffs still on my wrist. “Are you ever going to get the key and unlock me, or am I forever supposed to be your sex prisoner.” He smiled with this naughty little grin. He did call down to room service for the required specials.

  We lay there together in a post orgasmic glow and then there was that telltale knocking on the door. He leaped off the bed and went over to the door to fling it open. I tried to cover myself, but it was very difficult with my hands immobilized like they were. I managed to pull the sheet up far enough. The bellboy didn’t see too much of my considerable charms.

  “I’m going to give you this $20.00 tip young man, I want you to look at this woman and see the beauty that I see. She is a rare creature. I can never guess what’s on her mind, but I know she loves me with all of her heart. I’ve been getting closer to saying it, but I want you to be here to witness my declaration. I do love her and I would never let anything happen to her. She is all mine and no other man is ever going to touch her again.” The kid couldn’t have been more than 18 years old. He couldn’t take his eyes off my breasts. “I hate to do this to you, but I’m afraid that I’m going to have to ask you to leave in your current condition.” The bulge in his pants was very flattering.”

  He escorted him out of the room. He closed the door and gave me a look that said tonight had only begun. He continued to rise to the challenge three more times, until we were too exhausted to move. Thankfully, the steak and the lobster were good enough to keep us going. The champagne tickled my nose. I was not much for drinking. In the morning, we knew that our time together was just beginning.