justmeincal247
04-16-2011, 04:52 AM
First a bit of history; I had discovered the sensitivity of my ass while jacking off at an early age and frequently fingered my ass while jacking off. I did not have an attraction to guys and was a bit confused by this sensation but my ass would pucker whenever I would jack off so I went with it;)
So it was my 18th birthday and after partying with some friends, I was heading home, felling really horny I decided to pick up a Hollywood Xpress (Sex classifieds as this was pre-internet). Looking through the classifieds at the working girls, I suddenly turned to a page with TS’s which I was unfamiliar with and instantly got a painful hard on! This was perfect I thought, a beautiful woman with a cock that could really explore my sensitive ass. So I decided to give it a try and call one of the girls. The first girl, sounded rather manly and wasn’t too hospitable so I tried another. As I was looking through the pages, I spotted Mistress Monica… WOW she was gorgeous! She had long black hair, beautiful milky white tits and she was wearing a corset, stockings and leather boots. I had to call her! I nervously dialed her number and she answered sounded hot and sultry. I nervously said hello and told her I wanted to see her. She asked me what I was interested in and I explained that this would be my first time. She asked my age and I told her it was my 18th birthday, which she slightly chuckled at. She explained how this was a big step and that I should sleep on it and call her in the morning at 9:30 sharp if I was still interested and I agreed.
Upon hanging up, I lubed my finger and worked my needy ass as I stroked my cock until I shot loads and loads and fell asleep. All night I was restless as all I could think about was Mistress Monica. I woke up wanting her more than I did the night before and at 9:30 sharp….. I called her. When she answered the phone, she knew it was me and told me how glad she was that I called back. She told me I needed to douche before coming over and instructed me on how. As soon as I was douched and showered, I was to call her back
I rushed to the local drug store to pick up my disposable enemas and raced home to get the job done. Douching the first time was a bit awkward but somehow even that made me horny (oh the joys of being 18). Once that was done, I showered and got dressed and called her back. By now it was only 10:30 and she could tell I was extremely eager. She chuckled a bit once more when I called. This time she gave me directions to her house and told me that I must be very polite and address her as Mistress, which I quickly agreed too
I raced to her house and nervously walked up to her door and knocked. Then this beautiful woman in a long black robe opened the door and I was completely speechless. She smiled, said hello and grabbed my hand and gently pulled me into her house. She led me to her bedroom and told me to get naked and said she would be right back. Her room was dimly light and decorated in black and red, Her metal framed bed had straps at the head board and the foot of the bed. Just as I dropped my pants, SLAP,,, a barehanded spank on my ass as she walked in and caught me bending over. She chuckled as she said “we are going to have a good time” as I nodded. She instructed me to lie on the bed as she strapped my wrists and ankles. I was completely at her mercy. Even before she strapped me in, I was in such awe; she could have commanded me to do anything! At this point she was facing away from me and let her robe drop to the floor. I was staring at her beautiful ass in black lace panties and a black bra. She turned around and as I looked at her beautiful body, I saw a bulge in her panties that was actually rather huge and my cock just got harder! I was dripping like crazy when she asked me if I liked what I saw. I nodded and meekly said, yes Mistress. She slowly crawled on the bed and started sucking my dripping cock. She slowly but skillfully sucked like I had never been sucked before. As shed could tell I was ready to cum, she stopped an got up, she pulled off her panties and exposed a perfectly smooth cock that must have been about 8 to 9 inches and asked me if I had ever sucked cock before. I said no as she asked me if I wanted to suck hers, “yes Mistress I replied as she climbed back on me and straddled my body with her cock right in front of my face but far enough away that I could not reach it. I’m there wanting to suck this chicks cock more than I have ever wanted anything and she could tell so she teased me and mad me beg for it, then only rubbing it on my lips as I begged. She finally inserted her delicious dripping cock in my mouth. She tasted sweeter than I had ever imagined (although until that day, the thought of sucking cock never crossed my mind). As she got fully erect, she started pushing harder on the back of my throat and I actually felt my throat open up as she told me I was a natural and started to fuck my face. Her huge cock was penetrating deep into my throat and her balls were slapping my chin and I WAS LOVING IT!!! She was moaning as I was slurping and occasionally gasping for air until all of a sudden she stopped. She climbed off again and smiled at me, told me she would be right back and left the room. As I lie there strapped, I’m thinking what could be next? She was so amazing I felt like I came while sucking HER! She told me that for my obedience, she had a surprise, as she unstrapped me and guided me into the next room. The next room was some sort of dungeon and was filled with all kinds of toys and I was wondering what could be in store. In the middle of the room was this bench with straps hanging from the ceiling. As she led me to the bench, she strapped my hands behind me and my legs went in these straps the held them in the air. She then tickled me a bit as again I became fully erect. She then started licking my inner thighs, my balls and finally my needy ass, I moaning and groaning and squirming as she started to tongue my ass, she was driving me wild as she tongued me then inserted a finger. I was grinding on her face and finger and was in ecstasy. Then she got some lube and again inserted a finger as she gently sucked me. I was going crazy by this point as she prepped my ass. She then stopped and startled my face. Do you want me to fuck your tight ass she asked. Yes Mistress I said, show me as she shoved her cock in my mouth. I went crazy on her cock as she started to fuck my face and again with her cock fully erect she penetrated my throat and her balls slapped my chin. At that point she climbed off and got between my straddled legs. She pushed the head against my needy ass and told me to beg for it. Please Mistress I need to feel you inside of me. Beg bitch she told me. Please Mistress I need you.. LOUDER she shouted while she spanked me and inserted just a bit. PLEASE MISTRESS… FUCK ME I shouted as she pushed all the way inside of me. I took a deep breath as it hurt more than I imagine it would and she could tell by the look on my face so she pulled out. She then got her panties and soaked them in some liquid and told me “When I put this on your face, take a deep breath” Yea Mistress I replied as she again positioned herself between my straddled legs while pushing gently against my need ass. She then leaned over and placed her wet panties on my face. As I took a huge deep breath, I felt this big head rush as she pushed all the way in my ass. My head was still spinning as she started slowly grinding. As my head became clear again, she started slowly fucking me as I was moaning and really loving it. Beg bitch she screamed as she spanked me. On Mistress FUCK me, PLEASE I screamed as she started fucking harder and faster, harder faster, I was in another world as I asked her to release my hands so I could stroke my self. No darling, you are going to come like a bitch and when I tell you she commanded as she fucked me harder. Yes Mistress I am so close I yelled as she reached down and barely touched my cock, I started to cum like I had never cum before as she thrusted in me whit each shot. She then as I finished, she licked some of the cum off of my belly and came over and passionately kissed me at which I got hard again ☺. She released me from my straps and played freely with each other until she came once and I came again.
I actually called on Monica several more times and we had some amazing experiences. I still consider our sex to be the best I ever had… and that was 20 years ago!
So it was my 18th birthday and after partying with some friends, I was heading home, felling really horny I decided to pick up a Hollywood Xpress (Sex classifieds as this was pre-internet). Looking through the classifieds at the working girls, I suddenly turned to a page with TS’s which I was unfamiliar with and instantly got a painful hard on! This was perfect I thought, a beautiful woman with a cock that could really explore my sensitive ass. So I decided to give it a try and call one of the girls. The first girl, sounded rather manly and wasn’t too hospitable so I tried another. As I was looking through the pages, I spotted Mistress Monica… WOW she was gorgeous! She had long black hair, beautiful milky white tits and she was wearing a corset, stockings and leather boots. I had to call her! I nervously dialed her number and she answered sounded hot and sultry. I nervously said hello and told her I wanted to see her. She asked me what I was interested in and I explained that this would be my first time. She asked my age and I told her it was my 18th birthday, which she slightly chuckled at. She explained how this was a big step and that I should sleep on it and call her in the morning at 9:30 sharp if I was still interested and I agreed.
Upon hanging up, I lubed my finger and worked my needy ass as I stroked my cock until I shot loads and loads and fell asleep. All night I was restless as all I could think about was Mistress Monica. I woke up wanting her more than I did the night before and at 9:30 sharp….. I called her. When she answered the phone, she knew it was me and told me how glad she was that I called back. She told me I needed to douche before coming over and instructed me on how. As soon as I was douched and showered, I was to call her back
I rushed to the local drug store to pick up my disposable enemas and raced home to get the job done. Douching the first time was a bit awkward but somehow even that made me horny (oh the joys of being 18). Once that was done, I showered and got dressed and called her back. By now it was only 10:30 and she could tell I was extremely eager. She chuckled a bit once more when I called. This time she gave me directions to her house and told me that I must be very polite and address her as Mistress, which I quickly agreed too
I raced to her house and nervously walked up to her door and knocked. Then this beautiful woman in a long black robe opened the door and I was completely speechless. She smiled, said hello and grabbed my hand and gently pulled me into her house. She led me to her bedroom and told me to get naked and said she would be right back. Her room was dimly light and decorated in black and red, Her metal framed bed had straps at the head board and the foot of the bed. Just as I dropped my pants, SLAP,,, a barehanded spank on my ass as she walked in and caught me bending over. She chuckled as she said “we are going to have a good time” as I nodded. She instructed me to lie on the bed as she strapped my wrists and ankles. I was completely at her mercy. Even before she strapped me in, I was in such awe; she could have commanded me to do anything! At this point she was facing away from me and let her robe drop to the floor. I was staring at her beautiful ass in black lace panties and a black bra. She turned around and as I looked at her beautiful body, I saw a bulge in her panties that was actually rather huge and my cock just got harder! I was dripping like crazy when she asked me if I liked what I saw. I nodded and meekly said, yes Mistress. She slowly crawled on the bed and started sucking my dripping cock. She slowly but skillfully sucked like I had never been sucked before. As shed could tell I was ready to cum, she stopped an got up, she pulled off her panties and exposed a perfectly smooth cock that must have been about 8 to 9 inches and asked me if I had ever sucked cock before. I said no as she asked me if I wanted to suck hers, “yes Mistress I replied as she climbed back on me and straddled my body with her cock right in front of my face but far enough away that I could not reach it. I’m there wanting to suck this chicks cock more than I have ever wanted anything and she could tell so she teased me and mad me beg for it, then only rubbing it on my lips as I begged. She finally inserted her delicious dripping cock in my mouth. She tasted sweeter than I had ever imagined (although until that day, the thought of sucking cock never crossed my mind). As she got fully erect, she started pushing harder on the back of my throat and I actually felt my throat open up as she told me I was a natural and started to fuck my face. Her huge cock was penetrating deep into my throat and her balls were slapping my chin and I WAS LOVING IT!!! She was moaning as I was slurping and occasionally gasping for air until all of a sudden she stopped. She climbed off again and smiled at me, told me she would be right back and left the room. As I lie there strapped, I’m thinking what could be next? She was so amazing I felt like I came while sucking HER! She told me that for my obedience, she had a surprise, as she unstrapped me and guided me into the next room. The next room was some sort of dungeon and was filled with all kinds of toys and I was wondering what could be in store. In the middle of the room was this bench with straps hanging from the ceiling. As she led me to the bench, she strapped my hands behind me and my legs went in these straps the held them in the air. She then tickled me a bit as again I became fully erect. She then started licking my inner thighs, my balls and finally my needy ass, I moaning and groaning and squirming as she started to tongue my ass, she was driving me wild as she tongued me then inserted a finger. I was grinding on her face and finger and was in ecstasy. Then she got some lube and again inserted a finger as she gently sucked me. I was going crazy by this point as she prepped my ass. She then stopped and startled my face. Do you want me to fuck your tight ass she asked. Yes Mistress I said, show me as she shoved her cock in my mouth. I went crazy on her cock as she started to fuck my face and again with her cock fully erect she penetrated my throat and her balls slapped my chin. At that point she climbed off and got between my straddled legs. She pushed the head against my needy ass and told me to beg for it. Please Mistress I need to feel you inside of me. Beg bitch she told me. Please Mistress I need you.. LOUDER she shouted while she spanked me and inserted just a bit. PLEASE MISTRESS… FUCK ME I shouted as she pushed all the way inside of me. I took a deep breath as it hurt more than I imagine it would and she could tell by the look on my face so she pulled out. She then got her panties and soaked them in some liquid and told me “When I put this on your face, take a deep breath” Yea Mistress I replied as she again positioned herself between my straddled legs while pushing gently against my need ass. She then leaned over and placed her wet panties on my face. As I took a huge deep breath, I felt this big head rush as she pushed all the way in my ass. My head was still spinning as she started slowly grinding. As my head became clear again, she started slowly fucking me as I was moaning and really loving it. Beg bitch she screamed as she spanked me. On Mistress FUCK me, PLEASE I screamed as she started fucking harder and faster, harder faster, I was in another world as I asked her to release my hands so I could stroke my self. No darling, you are going to come like a bitch and when I tell you she commanded as she fucked me harder. Yes Mistress I am so close I yelled as she reached down and barely touched my cock, I started to cum like I had never cum before as she thrusted in me whit each shot. She then as I finished, she licked some of the cum off of my belly and came over and passionately kissed me at which I got hard again ☺. She released me from my straps and played freely with each other until she came once and I came again.
I actually called on Monica several more times and we had some amazing experiences. I still consider our sex to be the best I ever had… and that was 20 years ago!