0 comments/ 19241 views/ 7 favorites A Date With Sir By: AnimalisticNeeds I haven't seen him in a very long time, it's been about four years now. We had the most amazing sex, and I felt whole when he revealed himself as the Dom I have always desired. I haven't been this nervous since the first day I met him. We've both changed a lot, and been through ups and downs; quite frankly I thought I'd never see him again. You can imagine my shock when he told me we should meet. I hopped the first flight there and I am now preparing myself in my hotel room. I am not sure what to expect so I'm going to prepare myself for anything he may have in store. I got the bath water running in my hotel room so I could take a nice long, relaxing soak. I grabbed the bag of goodies I bought earlier and started tearing open the enema box. I have never successfully had anal sex, and quite honestly I didn't plan on ever having it unless it was with him. I was desperately hoping that he could show me the ropes tonight. After I got the box open I started reading the directions, I have never used one of these kits before so I was pretty nervous, but I wanted to make sure that if any type of anal play was to happen, I would be prepared and nice and clean for him. It wasn't as hard as I thought it would have been I just kind of lubed the tip up and slowly guided it into my ass. I emptied almost the entire contents into myself and waited the three minutes and relieved myself. When I was done with my enema I reached into the bag and grabbed the shaving cream and razors. I climbed into the tub and laid down for a few minutes letting myself relax. The water was so warm and comforting; I tried not to lay there too long because I was afraid I'd fall asleep. As I was laying in the water I caught myself daydreaming about what may happen that night. Were we really just going out for dinner and maybe some coffee after; or did he have ulterior motives? I was certainly hoping it would be more. "Oh well" I thought, "whatever happens, happens." On that note I started lathering up my legs and shaving them to a nice smooth and silky finish, then I turned the shaving cream on my pubic area. I lathered up my entire pussy and ass and shaved every last bit, I wanted to make sure there was not one hair on my body, just the way he liked it. Right as I was finishing up in the tub, my cell phone rang. It was him, he was just calling to verify what time he should pick me up. I told him that 6ish was good and I'd be ready when he got there. I then asked what kind of clothes I should wear so I wasn't too under dressed or over dressed. He reminded me he was no longer my sir and he would not tell me what to wear. "But I just want to know if I should wear a dress, or jeans and a t-shirt." "Wear whatever you want, we will pick the place depending on what you're wearing." Click, he hung up. "Fuck" I muttered to myself. A dress it is then. I picked out one of the cute white dresses I packed, it was a halter top that was a touch provocative. It covered my ass, but only by a few inches and I'm sure if I bent over just enough, some lucky guy would get a nice little show. I decided not to put any panties on because I enjoy feeling my bald pussy rubbing on the inside of my thighs when I crossed my legs. I continued to get ready, rubbing a nicely scented lotion on my freshly shaved legs, and then up to my arms. I let my long brown hair down, I always found it erotic when women with long hair wore it down. My hair is considered long, it is about two inches below my small perky breasts. I suppose I should tell a little bit about myself. I'm 22 and of Cuban and Italian decent. I am 5'5'' and though when he used to know me I was thinner, I am now a little bit on the heavy side, but not quite fat. I have small boobs, a 34A to be exact, pierced nipples, a nice ass, and my clit hood is pierced as well. Just as I was putting on my heels I heard a knock at the door. I looked over at the clock and realized it was almost 6 o'clock. "Oh damn" I mumbled I must have lost track of time. He's usually early when we make plans and I should have known better than to expect him after 6. I hurried up and finished putting on my high heels and answered the door. Oh my god, he is exactly what I remembered he was. Before I could even get a word out he said "Wow, you look great" and gave me a huge bear hug. He smelled so wonderful, all of my memories came flooding back to me when I smelled his shampoo. He totally took my breath away, I somehow managed to push out the words "hi gorgeous." and I saw his face light up. "You ready?" he said. "Yeah, let me just grab my purse and we can head out" With that he laughed and said "Purse? You never ever carried a purse before." "Yeah well, I'm not 18 anymore." "I know, I'll try to keep that in mind, it's just hard for me to remember that you've grown up." We got in his car and left. We made small talk the whole way to the restaurant and I kept catching myself looking down at his crotch. I wasn't sure if he had a chubby or it was just the way his pants were falling, but either way just looking in that area was starting to make me moist. When we got to the restaurant we sat down in a somewhat secluded area, and I asked him if I could sit next to him rather than across from him. He once again reminded me that I didn't need his permission for anything anymore. I guess it's hard to let old habits die. We placed our orders and continued on with the small talk, we caught up on things that have been going on and things that have gone on in the past 4 or 5 years. I was trying desperately to figure out if he had more interest in me than just talking as old friends. As we were sitting there I started to think about what had gone on that day and remembered that I wasn't wearing any panties, I apparently started to grin a little without even realizing it "what are you thinking about?" he quickly shot. It caught me off guard a bit because I wasn't expecting him to be paying so close attention to my expression. "Oh nothing, just thinking about how my day went that's all." "You always were a terrible liar" "Not-uh" I said, "I really am thinking about what I did today" "Really, so why are you smiling then?" Here goes nothing, I lightly grabbed his hand and placed it on my thigh,. I then moved his pinky finger towards my cunt very slowly just enough so where he lightly brushed against my naked bald pussy. He jerked his hand away in an instant and gave me a very disapproving look. I knew it was a gamble, and I guess I should have just played it safe on that one. It's obvious he didn't meet me with any intentions of fucking. So I apologized and quickly changed the subject. After about ten minutes of drinks and appetizers the mood finally returned back to being tension free, and then our food came. We ate our dinners and opted out of dessert. I asked him if we could go to Sonic's for old times sake and get a shake. He said that it sounded like a great idea and we went. On the way to Sonic's I couldn't help but to feel the sexual tension, maybe it was just me, maybe he was just being guarded, who knows. So feeling a little adventurous and tipsy from the martini I had with dinner, I decided I'd put my feet up on the dash and let the wind from the open window catch under my skirt and give him a quick little flash, all innocent of course. I did so and watched his eyes intently. As soon as I put my feet up on the dash I watched his eyes go from the heel of my shoes all the way up my smooth legs to my bald pussy. I smiled slyly to myself, maybe he's just playing hard to get. We finished our shakes and sadly he said we should call it a night. My heart sank, it was so nice to see him and spend time with him, I didn't want it to end, but I knew that he had to go home now. He dropped me off at my hotel and before he took off I asked him if I could at least kiss him. I could tell he was a little uncomfortable with my request but I gave him the best puppy dog eyes I could and begged a little more. He finally gave in, and we kissed. It was amazing his lips were so soft and his tongue massaged mine with an incredible expertise. As we kissed I could feel my pussy getting warmer and wetter. My clit started to swell a bit and then everything began to throb. I had to pull away from him because I knew that he wouldn't be staying the night, and just as I turned to leave I could feel a drop of moisture run down my leg, and he jokingly said "look at you slut, you're dripping." And with that he turned toward his car and left. My mind was racing. Did I hear him right? Did he call me slut again? There was no calming my aching pussy at this point. Calling me slut was a surefire way to make me lose my mind and he knew that. I ran to my suitcase and pulled out the vibrator I had packed. I didn't even bother taking off my dress, I just kicked off my heels and jumped on the bed. I wanted this moment to last so I took my time slowly seducing myself with the vibrator off. I licked it and sucked on it, imagining it was him. I didn't even need to wet it because my pussy was dripping as it was, but I was really longing for him in my mouth. I took the vibrator and brought it down to my pussy, I slowly massaged my outer lips with it, teasingly dipping just the tip in every now and then. I turned it on low and rubbed it up and down my wet slit, every so often brushing my clit with it and feeling the vibrations throughout my body. I knew I was going to cum soon so I turned it off and licked it a couple of times. I wanted this to last a little. Suddenly there was a pounding on the door, I nearly jumped off the bed. I was so involved in what I was doing the sudden disturbance nearly gave me a heart attack. I quickly opened one of the dresser drawers and threw the vibrator in it and glanced at myself in the mirror to make sure I was somewhat presentable. I answered the door and it was him. "What are you doing here?" I asked him, extremely nervous. He pushed his way past me and shut the door, not even bothering to answer my question. When he came to the door I was so startled, I didn't even notice he had a backpack with him. He sat the backpack on the table and said very forcefully "get on the bed slut." I started to protest and then I saw the look in his eyes. I had no idea what was about to happen, but I was trying to decide whether I should obey or disobey, as much as I enjoy serving and obeying, I enjoy the occasional punishment even more. "I'm not going to tell you again slut, get on the bed" And on that note I climbed on the bed. "Sit there while I get some things out of my bag. So you think you're cute trying to seduce me at dinner don't you? You think it's fun to show me your pussy in the car when you're trying to act innocent." "No sir." "Don't lie to me, you're a slut and you can't help yourself. All you can think of is how I'm going to fuck you and how you're going to love it. You don't even care that you walked out of my life for five years, you just want to be a slut." "That's not..." "Shut up slut, you came all this way just to get fucked? Then you're going to get exactly what you came here for" He then came over to the bed and said "give me your hands" I put my arms in front of me, and he quickly put a pair of bondage cuffs on me. He then proceeded to put some around my ankles as well. He walked back to his bag and I saw him take out two spreader bars. "You don't need those, I'll be good I promise." "Trust me slut, I need them. When I shove my cock in your ass I know you won't stay put, so I need to make sure I have the right equipment" My pussy instantly flooded again. He was going to take my ass! This is something I've wanted for years, something I have been saving just for him if the chance ever arose, and now it was coming to fruition. I couldn't believe it. He put the spreader bars next to me on my right and then he laid next to me on the left. He grabbed my face and kissed me deeply. Then he said "I've missed your pussy and your mouth tremendously, and when I'm through with you I'm going to miss your ass too." This isn't going to be the last time, I thought to myself, at least I hoped it wouldn't be. "Have you missed me kitten?" "God yes, every time I fantasize, and masturbate I think about you, every time I hear music I relate the lyrics to you. You have been on my mind forever and I don't think that will ever go away." "Good girl. Have you missed the taste of my cock and cum?" "Yes I have, I can't wait to taste your cum again" "Yes what?" I quickly blushed at my forgetfulness "Yes sir" I said. "If you forget again kitten, you know the rules" "Yes sir" I said shamefully. "Now hop down and get on your knees, and pay my cock some attention, it's been years since I've felt that wonderful mouth of yours and it would be great to feel it now." I quickly got off of the bed and pulled his pants down, I held them at his ankles so he could step out of them. He wasn't wearing any underwear and I was staring directly at his gorgeous cock. He was so excited that there was precum dripping from the tip, I wasted no time licking it off. Mmmm it tastes just how I remembered it. I licked the head of his prick slowly, teasingly then I licked the length of his shaft and down to his balls. I slowly took one, then the other into my mouth, caressing them with my tongue. I wanted to savor every inch of his manhood, from balls to cock. I licked back up the underside of his shaft and took his head into my mouth. I reached up with my hand and started playing with his balls, caressing them gently. Then I started sucking softly and taking the entire length deep into my throat. I don't have much of a gag reflex so I shoved as much in as I could take, tasting and swallowing every drop of pre cum that came out of that amazing cock. I sped up my pace a little until I could feel his balls tighten then I moved my hand from his balls to his shaft and stroked with every move of my head. He quickly grabbed the back of my head and started fucking my mouth faster and harder. I knew he was going to cum soon and my pussy was dripping at the thought of his hot cum running down my throat. "I'm gonna cum bitch are you ready to catch it?" "Mmhmm" I moaned with a mouthful of cock, the vibrations of me trying to speak must have sent him over the edge because in a split second my mouth quickly filled with cum and it started dribbling out of the corner of my mouth. "You better not spill any" I quickly caught whatever seed spilled out of my mouth with my finger and licked it clean. I swallowed every last drop and grabbed his cock and licked the entire length and the head to make sure none was still on him. He gently stroked my face and gave me a look of satisfaction. He didn't need to say a word, I knew he was happy with me. "I'm gonna rinse off, be on the bed in your position before I get back" As soon as he went into the bathroom I climbed on the bed and got on my knees facing the wall with my hands behind my back, and my eyes down. I waited there oh so patiently but just the anticipation of what was to come had my pussy throbbing and dripping into a newly formed puddle below me. A few minutes later he came back into the room. "I'm pleased to see you remembered your position" I heard him rummaging around in his bag and when he found what he was looking for he came to the bed. "Open your mouth" I opened my mouth and he put a ball gag in and fastened it tightly behind my head. I was incredibly nervous, I've never had a ball gag in my mouth before and I was terrified that I wouldn't be able to let him know if I was reaching my limit. At least I had my hands, I could push him away if I needed to...or so I thought. He then spread my arms wide and hooked my wrist restraints to each end of the spreader bar that was laying on the bed. "Spread your legs" I was too busy worrying about how I was going to stop him from doing anything that I didn't want him to do, that I didn't hear his last command. SMACK he slapped my ass hard with his open hand. "That was a warning, spread your legs" I immediately did and he quickly clipped my ankle restraints to the other spreader bar that was on the bed. He pushed my face down into the bed so I was on my knees in a bent over position with my ass in the air and my face to the bed. He could see every inch of my pussy and ass from this angle, and I was feeling very insecure and vulnerable. SMACK he slapped my ass with his bare hands his fingers just barely grazing my pussy. "You have no idea how long I've been wanting to do this. I've been wanting to punish you for leaving me for four years now." SMACK another hard slap to my ass, I screamed into the ball gag but it was no use. I haven't been spanked in a very long time and I was not used to the pain. As much as it hurt, it made my pussy flood. SMACK "You think you can just waltz back into my life like nothing happened?" SMACK "Well you can't, not without at least being punished anyway." SMACK SMACK SMACK SMACK SMACK I thought it would never end, my ass was burning and yet my pussy was soaked. Finally he stopped with the spankings and rubbed my aching ass. It felt so nice and soothing. He then started licking and kissing all the places that were now bright red. I moaned into my gag. It felt incredible. He then started to slowly lick my slit, licking up all the juice that was now running down my thighs. He fucked my pussy with his tongue for a minute then wandered to my clit. He teased it sucking on it for a second then biting softly then licking my swollen clit. I wanted to cum so bad, but I knew I didn't have permission, and I also knew it would feel much better if I came on his cock. As he was playing with my clit with his mouth he took his finger and started stroking my pussy, pushing his finger half way in then pulling it out. I wanted to feel his finger in me so bad I pushed my ass towards his finger. SMACK. "Don't move slut" He moved from behind me and laid next to me on the bed. "Sit up you whore I wanna see your tits" I quickly used my shoulders to push off the bed and sit straight up. "I can't believe you got your nipples pierced, you know I'm not going to be able to resist torturing them" My eyes widened quickly. I was terrified that he would be too rough. "Don't worry slut, I didn't bring the proper equipment, but I'll get my chance some other time I'm sure" He quickly took my left nipple in his mouth and started sucking hard. He ran his tongue all around it and then licked down my tit and back up to the nipple. He then did the same to the right nipple until both of my nipples were rock hard and standing at full attention. "Beautiful" he said staring at my tits. He then pushed me roughly back down into the position I was in before. He came around back to my pussy and ran his finger up and down it. "You're completely soaked, is that cause you want my cock?" "Mmmhmm" I managed to push out around the ball gag. He then took his prick and started teasing my dripping cunt with it. Rubbing back and forth while paying close attention to my clit. He then slowly put the head in and then took it out and started rubbing. It was almost too much to take. All I wanted was to feel his cock buried deep in my pussy, but I knew better than to move so I just sat there and took the teasing. Finally in one huge stroke he sunk his cock deep in me and started fucking me hard and fast. All I could think about was how heavenly this felt. He slowed down his pace a bit and as he did that I felt my pussy tense up. Oh no, I thought, I can't cum, not yet, he hasn't given me permission yet. "I can feel that your pussy wants to cum. Do you wanna cum slut?" "Mmhmm" "Ok slut, you can cum on my cock" He picked up his pace and started fucking me fast and hard again and in a matter of seconds I was cumming so hard I thought I'd bite the ball gag in half. A Date With Sir When I was done cumming he pulled his dick out and started stroking it slowly. He bent down and licked my ass. "I hope you're ready for your tight little ass to get filled tonight." My moment of joy turned into a moment of sheer panic. I know I've wanted this forever, but I'm so scared it's gonna hurt. He lowered his head again and started teasing my asshole with his tongue. He licked it slowly trying to push his way in, and making sure he was lubing it up very nicely. He moved his head lower and started working on my pussy. He took his finger and started playing with my asshole, slowly pushing it in a little ways, then taking it out. He then pushed his entire finger into me and let my ass get used to it. Then he pulled it out and slowly worked in two fingers. When he felt like I was relaxed enough he put his cock into my pussy getting as much as my juices as possible on it. He then slowly brought the head of his dick to my ass pushing just the tip in. He sat there for a minute letting my ass get accommodated to the size. He then pushed a little further in. I screamed into my ball gag. It was the sharpest, most excruciating pain. Seeing as I was tied up and gagged, I couldn't go anywhere and surprisingly, after a minute of him staying still, it didn't hurt so bad anymore, in fact it was starting to feel good. "OK are you ready?" With that he sunk his cock in my ass, balls deep. I clenched my teeth hard on the gag but it wasn't as bad as my past experiences. "God your ass is so tight, I'm so glad I'm the one who gets to enjoy this first" Hearing that made me want to smile. It warmed my heart for a minute, and then he started pumping my ass. Slowly at first, but then he picked up the pace. His breathing became heavier and I could tell he was close to cumming. "Ok slut I'm going to fill your ass with my cum. I hope you're ready. And you have my permission to cum" I came instantly at the sound of his words. He slammed his cock deep into me and held himself there. I could feel his hot cum in my ass, it felt incredible. I can't remember anything I have ever done that felt as good as that did. He stood there for a few minutes letting his cock soften and fall out of my ass with an spilling a little seed with it. He then took all of my restraints off and the ball gag out of my mouth. "You did very good kitten" he said. "Thank you sir, that was amazing." He then took my face in his hands and kissed me deeply. I closed my eyes and tasted the remnants of my pussy on his lips and in his moustache. I love it when he calls me kitten. And for a while there I felt like I was in another world. He then laid down and I laid next to him and put my head on his chest. "I'm not done with you yet kitten, but let's take a nap first." I just smiled and drifted off to sleep. A date with Stunning Summer I spend some time with the internet porn star and fulfill a fantasy. I'm a young guy in my mid 20's who just happens to have a fetish for mature women. I just think they are much sexier and more desirous when they are 40 and up. Since this is my preference, I scan the internet and look at all the granny and MILF sites. That was how I discovered Stunning Summer. For those that know of her and have the same desire as me, no explanation is required. For those that don't know of her, she is an internet porn star who happens to be in her late forties. She is blonde, with nice blue eyes and a pleasingly plump frame. She is about 5'4 but looks smaller as she fills out in the right areas. Her tits are 36DD, and those amazing hips are 37. She has a website where you can "donate" for her services. Services include everything from social interaction to personal attention. Also on her site are pictures, videos and the like outlining what she offers. But it was other sites that offered a more compelling look at this lady. Summer is hot in the sack. You can tell even though she is an actress, that she really likes what she does, and her reactions are true. A number of sites have her with multiple hung black guys who put her thru the paces. She can engulf almost any size cock in any hole and not flinch. She takes internal shots as well as splatters to the face with tongue cleanup. The way she can ride a cock is awesome with her plump ass bouncing and moving the way it does. You can tell that it affects her partners as well and they strain to hold back from blowing their loads. I am not naïve to believe this is all real, but I think one can tell if people are going thru the motions or are enjoying themselves, Summer is enjoying herself and it is infectious. Well about 4 months ago, I got a call from a lawyer who informed me that my uncle had passed away suddenly in an accident. After adsorbing the shock of the news, he told me that I was the sole beneficiary of my uncle's estate and could I come to California when the probate would start. I went out there and discovered that besides a nice mortgage free home near San Diego, my uncle Dave had also left about 200K after debts. Not having much money myself, this was a jackpot. It was at this time I made contact with Stunning Summer and set up a date with her. I met Summer in a bar of her choosing and was awed when she came in with a black cocktail dress on that highlighted her cleavage and those hips and ass. Stunning was really the word for her. She was a delight to talk to over several drinks, very knowledgeable over various subjects. We finished up and headed back to my hotel. Once the financials were finalized, Summer did a slow strip tease and gradually exposed that hot body that I only had seen flicker on the computer screen before. She was an excellent kisser and things progressed slow and with passion. This woman knew how to ooze out passion and heat. She began to work on my dick and proved to be the most excellent cocksucker I've ever encountered. Her pussy and ass opened up to my probing fingers and I had a slight concern, based on the size of my equipment, that I would be able to fully enjoy this experience. I am about 7 inches and some of the guys on the internet were almost twice that and far thicker, and she required little effort to accommodate them. I had nothing to worry about, as Summer proved to be most adaptive. Her pelvic action could be like a vise on a pen. My dick felt like it was in a recently broken in virgin. We fucked slow then hard and then frantic. I got to enjoy her pussy, ass and mouth. But the highlight of my night as well as my fantasy, was when Stunning Summer sat on my lap and did the gyrations and bouncing on my dick that had me mesmerized since the first time I saw her on the computer. She allowed me to come inside her bareback and I thought all the fluid in my body was flowing out. I had one more experience that night before we called it quits. I am grateful for the experience and still email Summer for a possible repeat when I get back to California. I got to live out a fantasy into reality. I hope you can have the same one day.