Older Male / Female

Sinnndy Meets Billy

Summer hijinks starting with my vacation, and then going out with Billy. I was 18, he was 31, there was immediate heat and there still is today.

Dating Once Again

Shortly after being divorced for several years, death in the family and the disownment from a family member, I felt so alone and that my world has turned upside down. I haven’t been dated since my divorce and I am a highly sensual but fairly attractive woman. Short, stout with dark eyes, dark hair. 56I-46-44. Very much old fashion where I love to meet guys in person, but since my divorce, Which by the way, I have been happy before, during and after my divorce. So I tried this internet dating but I was so hornier then ever. Met a couple guys on-line where we chatted by instant messaging for about a month or so. A bit hesitant to meet these guys though I am a very busy person. One guy was within my age group while the other was old enough to be either my father or grandfather. I have always has this fetish of dating guys slightly older than I am. I am a bit shy especially when I comes to sex, though I may explore outside of my comfort zone since I am naturally submissive with a touch of kink. At any rate, I decided to date the older guy who is old enough to be either my father or grandfather. His name is Gerry.
The minute I met him through cam to cam, I decided to meet him in person. He was very kind and gentle that I wanted to be with him. He wasn’t pushy at all. It was a nice hot summery day when I got into his jeep, drove around to get acquainted. As we were getting acquainted he wanted to get very familiar for which I was comfortable of doing. So we got in back in seat of his jeep where we kissed and felt one another discretely in a mall parking garage out of sight of the camera and mall security probing the area. I wore a button down dress with several buttons unbuttoned down to my cleavage without a bra and a white bikini pantie.
As we were kissing, touching and fondling one another, his kiss got so deep that I had to submit to whatever came natural. He placed his hand on my left breast and started caressing it as he unbutton the rest. He opened the dress and he was amazing of my big breast that he wanted to examined them. Brown breast with dark milk chocolate mid-sized nipples that were standing so erect ready to suck on. He took my left nipple to suck as he caressed my right nipple. While he was doing that I was getting so moist and was curious whether he was either a boxer or brief kinda guy. He took his time to caress and suck each of them. then took both of my breasts to suck them both together. While he was busy with my breasts, my hand was on his crotch. He moved back to my lips for a kiss as he scooted my moist white bikini off to see my pussy in full view. Brown with very little pubic hair covering the opening of my pussy . He slid his fingers on my slit as I continue feeling his crotch. He realized that I was very wet that he wanted to taste me. He got down on the floorboard and spread my legs wide and started to eat me out. I had never had my pussy eaten out. I was sold. We only met for almost two hours before he had to leave as well as I had another date to go to. He didn’t want me to go and wanted him all to himself.
Several weeks has past and we met again where we drove to the same spot, but this time he had the back seat down in the back. He was very excited to see me once again and wanted to be serious with me, but not too serious, but a steady relationship. He was deeply in love with me that he wanted more as well as I did. I could see it in his eyes that he was deeply in love with me. His kisses became more compassionate. He had great joys of getting naked but this time it was his time to reveal himself. I played with his cock as he craved for my pussy juice. He didn’t rush to do the 69, but took his time as he wanted to get to know who I am as a person while petting, caressing every inch of my body. He took time to listen who I am as person. He pulled my face much closer for a much deeper kissing as he began to undress me. Laying there completely naked in back of his jeep, he was in full view and love me even much more. He kissed every in of my body, sucked my nipples as he fingered my pussy. Slowly moving towards my pussy, he enjoyed the way I was squirming and jumping like a fish as he played with my clit and chatted some more. I was getting so soaked that he didn’t want to wasted the wetness that would be soaked into the carpet so he dove toward my pussy to savory my juices. Then I said, it is your turn as he undid his pants without any underpants. He had a male issue, but that didn’t as much. I wanted to feel him inside my mouth. He was just firm enough but not hard which he felt bad about it. He was an average size and average width. From that time we did 69.
We continued seeing one another and he had the courage to ask me to go with him for monthly day trips to keep him company. I was much obliged to accompany him for his monthly day trips which lead into overnights. Then I knew that he wanted to get serious with the relationship where he asked my likes and dislikes and it ended up a very long term relationship.

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Encounter with Uncles (Revised)

When I was about 22 years old, my girlfriend and I were talking about one of her relatives in particular, her uncle. I might have been buzzed from drinking vodka and seven-up/sprite when I said that her uncle was hot. I have seen her uncle and I wanted him. Seeing him for the first time was instant attraction. I innocently in a flirtatious matter held and lifted my big breasts to him. She made a call to her uncle said that we were coming over and took me over to her uncle’s place. I kissed her uncle which was nice and her uncle graciously kissed me back. As he was kissing, he took his hand to touch my breasts. He asked me to unbutton a few buttons for him, so I did. He kissed me more deeply as he removed the blouse and was in hurry to take the bra off. I stood before him half naked. He grabbed my hands and pulled me to the couch to sit next to him. He took my breasts where he grabbed, pulled, pinched, sucked them. After he was done he pulled my pants and panties off. He suggested that we should go to the bedroom but we should take a shower first. Innocently, I said,”Shower with you.” Both my friend and her uncle said “Yes, don’t worry, I won’t hurt you, you are so sexy. The next thing I knew I was in the shower with him and going down on him in the shower. After he had cum, he dried me off and carried me to his bed.
I must have fallen asleep but he woke me up as he ate my pussy and sucked my tits. Though it was real, it felt as if I was dreaming. I was really buzzed and I fell back to sleep on him after he fucked me, which felt good. The next morning I had to call my girlfriend to ask her what happened. She laughed as she told me what happened and it was a funny but serious sexual experience, but I vowed to myself that I would never drink alcohol before a sexual experience so I could remember it and be aware of what was happening. I felt so very sexy that a much older man wanted me and that having sex with my best friend’s uncle was so hot.
When I was about 17-18 years old, I was alone with one of my uncles. We were in their bedroom setting up their new bed. He either, accidentally or purposely brushed his hands against my breast and asked me how big they were. Feeling awkward and uncomfortable, I got angry. He is one of the hottest uncles which I grew very fond of and excited by the pass he made. It is a fantasy that I regretted and kept as a secret from the family. If I were to submit to his pass, I would have answered his question, I would have allowed him to touch, feel, see my breasts, I would have been topless and would never said anything to anyone. At that time, I was a 36D.
Close to their divorce, I wanted so badly to rekindle that afternoon with him. This time, I was in my late 30’s. I was alone with him, but did not know for how long. Therefore, I would fantasize how he would take it, me standing naked before him. I wanted so badly to expose myself to him. Allow him to see, view my breasts and do whatever he pleased. I also wanted him to do the same with my vagina. Without a doubt, I wanted to see, view his penis and have his penis in my vagina.
Many times I was in their bathroom and wanted so badly to shower in their clear glassed shower and get caught by him. I wanted to have him in the shower with me. When I was alone with him in his office, I fantasize him telling me to remove my top or having him come behind me to feel my breasts. I don’t see him too much anymore, but when I do, I managed to either brush or bump into him with my breasts discretely. He may notice it but never mentioned the brush or bump bothering him.
This is a fantasy: If he were to walk into the bathroom while I was in there. I would not mind him seeing me naked, but I would say to him lock the door. I would kiss him, and it would not be a peck in the cheek. I would confess to him that I have been lusting over him for years and take his hands to my breasts and cupped his penis through his pants. Tell him that he has always been my favorite uncle and have not forgotten about his question while we were setting up his water bed and want to make it up to him by servicing him.
Then I would try to set up a date with him and tell him all of my fantasies that I had about him where I have never stop thinking about it. This goes so far as submitting and having intercourse with him. I would not even wear a bra and panties, but wear a very short skirt and white tee-shirt. I would intentionally pour ice cold water on my white tee-shirt so my nipples would be completely exposed for him to see. This would entice him to make advances to me. He would unzip his pants to expose his penis and demand for me to service him like a good niece would. He would say that my brushes and bumps was a complete turn on and for me to keep continuing to do so. He says that I was one of his favorite nieces and admitted that he also has fantasies about me and having sex with me and that he always will love me.
As for now he wants to caress, fondle, touch, and feel every inch of my body as I suck and lick his penis. He wants having sex with me to be very special where he wants to buy me the sexiest dress, a bra, a pair of panties, a sheer nightgown, and then wine and dine me for an entire weekend. We vowed to never mention this to the family.

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~*~A year later….~*~

I was sent away for awhile, Daddy said I need to be taught how to listen…since in a resturant ( that daddy owned), I broke out crying and asking for help. We were in a booth a very private booth, so nobody could hear me. I got punished for that, not sexual but physical. I got sent to an all girl boarding school. Being at boarding school really sucked sorta, I was forgotten for a year, not a word form him…just presents at Christmas and my birthday. So to me this was heaven since I am far from him. I have given up utter hope of him coming back for me. A week later I was wrong, Daddy sent his assistant to come and get me. After a week of up-dating my wardrobe and hair style, I was sent to a France. The limo picked me up and drove me to counrty of France too a big French Villa that over looked the sea. Another assistant told me daddy was going to be a few day late, so to me I was happy. Surprise…surprise…Daddy was there.
** “Ahhh…my little angel, how you have grown in a year!” Daddy whispered more to himself then me, “Have you learned your lesson?”
Turning to see if the assistant was there, but she was gone and the door shut, “Yes.” I replied looking around worried.
I forgot how handsome and young daddy looked, then a his courtier smile spread across his face, like he knew what I was thinking. Gulping, I looked at him and smiled sweetly, that was all, I didn’t want ” it ” to happen again! I try to forget that first day I came to him, and…what…he…did…and…umm…what…what I felt.
The face I hoped I wouldn’t see came over his handsome face, his malicious look, the same look…before…
“Come over here little girl!” Daddy ordered. Slowly walking over to him, he grabed my arm roughly.
“Ouch Daddy, let go!” I cry but he drags me to his study. Throwing me onto his couch, he quickly starts to undo his belt and un-zip his pants, letting them drop. Grabing and hand full of hair, and pulled my head level to his cock. Looking up and him, he was looking down at me, looking into his eyes, I saw pure joy wash over them, grabing my cheek between his hands to force my mouth open. Smiling big, he forced his cock into my mouth making me gag. “Baby! Suck daddys cock!” he whined,”Come on suck!”
Not sucking, made things worst. Grabing both sides of my head, he started to force my head back and forth, back and forth making my mouth move along his long thick cock. After a few moments of this, he shot his load into my mouth making me gag more and cough.
“Daddy ain’t finished yet sweetums, daddy wants to look at your body to see how much you’ve grown!” he hald moaned.
Pinning me down on the couch, he started to rip my clothes off until I was just in my white panties.
“Oh baby white…like a virgin…mmm…”he groaned
Making me stand and turn around to look me over, he jacked off.
Not looking at him, he came up behind me and grabed me. Turning me toward him quickly he picked me up and threw me over his shoulder. Screaming for him to stop and put me down, I didn’t realize we had moved to a room with a bed.
“What about my step-mom, don’t you love her!!” I sobbed
Throwing me on the bed, looking at me with his cold and warm eyes, he calmly told me he had divourced her. Crying harder, daddy crawled onto the bed and slowly toward me. Crawling closer to the bed frame to get away from him, he grabed my leg to hold me. Climbing up ontop of me, I tried to move away from him and squirm. Old memorys of last year flashed through my mind, so I froze up again. Feeling his cock lightly touch my pussy made me fight back with all my strength. Putting up a good fight, and making daddys lip bleed, he finally got my hands together. Scared, I cried sorry to him, but when I peered up at him, a smile I’ve never seen before was across his face, more evil then the last.
“So darling you like it like that do you…I’ll give it to you like that!” he moaned
His body between my legs and his cock pushed against my pussy, I cried harder then in one hurtful push, his cock was in me. Slowly but roughly he pushed in and out, then using his belt he tied my hands to the bed frame and lifted my legs over his shoulders.
“My poor little almost virgin, not been fucked in a year…little virgin, this is going to hurt more then ever, I’m not going to be so gentle!” he groaned, ” I’m going to make you scream louder and bleed longer tonight!”
Roughly forcing his cock deep into my sore pussy he started to push it in all the way hard as he could then pull out just to the tip and pound it back in, making me moan out and scream for him to stop.
“Darling its your fault, souldn’t have fought me!” he whispered sweetly
Pulling his cock out of my pussy, which was sore and slightly bleeding, he turned me onto my stomach and pulled my ass into the air, and pulled my legs apart just a little. Putting his hand on the back of my head he slowly moved into place behind me! Realizing what he was about to do,I started to cry out stop!

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Master and Slave

It was times like these that I counted myself lucky. I had disobeyed him, not on purpose, but it seemed he had forgiven me. I was waiting for him to tell me I could come in and suck his throbbing cock. Lord knows I wanted to give my best to him for giving me another chance at being a good sex slave. I sat in my car waiting, patiently waiting and counting myself lucky again. I was wearing something special beneath my regular clothes, something no one else had ever seen. I hoped he liked it. When the phone rang it gave me a chill and reached for it grabbing and just as quickly answering it.
“ Hello?” I said into the phone.
“ Come up here now, my little slave. This is where you will receive your punishment for being a disobedient slave. So hurry up to the room now.” He clicked the phone off.
It had never come to my attention that I would be punished. Guess it should have. I got out of my car and began walking to the hotel, going in the doors I looked around myself at the red carpet beneath my shoes. High heeled black shoes, the kind that would turn any mans head. I went to the elevator and pushed the button that would take me up to the third floor and to his waiting arms. I wanted his cock, wanted to feel it again. I remembered telling him before, how I thought each time I saw his hard member it always seemed to get bigger. Which filled me up more then before, it was a wonderful feeling. It made me feel like I was high, only this high was a lot better. I had someone making me feel this way. The elevator came to the floor and opened its doors, I walked in and pushed the number 3 that would take me to him. It stopped again on the second floor and a man walked in and winked at me. I just smiled back. The third floor came and we both got off, he went one way and I went another. I got to the tan door with the number, 315 on it and knocked. He opened the door and I walked in and smiled at him.
“ You disobeyed me, my little slut. Now for your punishment. First off, go wash up.” He had always made me jump in the shower before we did anything. I didn’t mind, it was fun. He would always come in after I was in the shower and start playing with my tight pussy.
“ Yes Master, as you say.” I started pulling my clothes off, revealing the black skimpy outfit beneath my clothes.
He slapped my ass, hard as I bent to take my panties off, making me squeal as he did so. I turned to look at him and he pointed to the bathroom. The light was already on, I went up to him and rubbed his chest in a teasing lingering kind of way. Then turned and started walking towards the bathroom, he slapped my ass, hard, making me jump as I walked off. I turned the water on and stepped into the shower. It was a nice warm temperature, it felt nice to be in the shower again. I washed up everything, touching my shaved pussy with the wash cloth and then rubbing around to my ass. I was taking my time. Thinking he was going to come walking in, I started rubbing my clit, I was getting so aroused just thinking about his hard cock and how fast and furious he would slam it into my tight wet, waiting pussy. In my mind I knew I should stop, I could make myself cum doing this, he had not said I could do that, it would be another thing I disobeyed him on. I removed my hand, my clit throbbed unmercifully, saying I had been close to cuming, I wanted so bad to reach back down there and continue. Then he came in and shoved the curtain aside. Still fully clothed, I was a little embarrassed, which was not normal, to be the only one naked.
“ Hurry up slut. I didn’t say you could take a long shower. You look clean.” He looked at my shaved pussy, he wanted it to be furry but it didn’t grow fast enough. Another thing I had disobeyed him on. He reached his out and slapped my pussy causing me to jump again. “ Let’s go.” he shut the water off and waited for me to get out and grab a towel.
I walked out of the bathroom, all dried off now and wrapped the towel around me. He grabbed the towel from and flung it back to the bathroom, he came to me and brought his lips down to mine in a possessive kiss. Demanding, I reached to touch his cock through his pants but he just as quick slapped my hand away then stopped kissing me and turned me around. My back was to him and he held me tight to his chest, his hands reached down to my pussy, he started playing with my clit making me feel dizzy with excitement. When he shoved one finger, then another, then another, I thought I would fall down to the floor if he hadn’t held me so tight. Then he pushed me away and I knew what was next. My punishment.
“ Get on the bed, bitch. This is for not listening to your master. Like you should have.” He watched me climb on the bed and lay down on my back. He went to the top left corner and grabbed a rope, tying my wrist to it. Then to the bottom left corner and tied my ankle to that corner. He did the same on the other two corners. I pulled at the ropes a little bit, he hadn’t tied me up before and I was a little nervous about what he was going to do. One thing I knew for sure, he wouldn’t hurt me. He was my master, I loved my master as I was sure he loved his slave.
“ Now my little slave, I am putting this vibrator on your clit. You are going to cum, over and over, but first you must ask every time. When I feel that you have had enough I will shove my cock inside your tight pussy.” He put the vibrator on high and I squealed with it just barely touching my clit. He slapped my clit and walked away, pulling his clothes off piece by piece.
I lay there as the pressure began to mount. I started squealing, this was torture! I wanted his cock inside my pussy, not a vibrator playing with my clit! I whimpered again and he looked over at me. He stood up and came walking over, he looked down at me and slapped my boobs, then grabbed one of my nipples and squeezed hard. Making me whimper, with pain and pleasure.
“ Master, master please. I’m going to cum. Can I cum, please master?” I begged, I was trying so hard to keep quiet but the moans kept coming. I had no control.
“ Hmmm, should I let you or not?” He saw my face, I was holding it back. The pressure had built until I felt like I was going to explode.
“ Please, master! I am going to…..explode! I need to cum, please?” I begged again. The pressure kept mounting as I kept fighting it back. The punishment for cuming before he said to, he still kept to himself. I didn’t know what that punishment would be. I didn’t want to find out.
“ Yes, slave. Yes my little bitch, cum for Master.” He grabbed my nipple again and squeezed hard as I let out a loud cry of pleasure and I came at once. He removed the vibrator and stuck a finger inside my pussy, then another and another. Three fingers were going in and out of my tight pussy, stretching me. I had no control still, my pussy throbbed from all the attention she was getting, the moans came louder, quicker as I was about to cum again.
“ Master?”
“ What my little love slave?”
“ I…..can I cum? I feel so close again, please?” I begged him and he slammed his fingers inside my pussy, deeper. “Oh god! Please, master, please?”
“ Yes, cum my little bitch. Cum!” He shoved his fingers in again deeper, making me cum as the pleasure exploded all over his fingers. He then climbed up on the bed, his thick hard throbbing cock positioned right about my mouth, and then he pushed himself inside my mouth. I greedily sucked on his cock, making him harder. My pussy was wet, wetter then she had ever been before, and sucking his cock was making her wetter. I sucked him until he pulled away and began untying me. I got up and he pushed me back down on the bed, with a look that said he didn’t tell me I could get up.
“ Get on all fours, bitch. Do it now!” He commanded me to do. I got up and was on all fours as he climbed up on me and shoved his cock into my tight, wet, waiting pussy. I screamed with pleasure, and a little from pain, he slammed it in all the way. It felt so good, he was in there so deep. My mind was running with feelings. He looked at my face and then reached and grabbed my nipple as he plunged in and out over and over again, I was still moaning, I couldn’t stop. It felt so good to have him deep inside me.
“ How does it feel bitch? Tell me, tell me it feels good.” He demanded me to speak, but my tongue was tied. I couldn’t say anything. And when I didn’t respond he slammed his cock into my pussy again. “ Speak bitch, tell me it feels good!”
“ Yes…….master…….it feels……so good!” I panted out, between breathes. It was so hard to talk as he slammed into me over and over again. I was loving every minute of it. I wanted his cum so bad.
“ I’m gonna cum bitch. And its going to be in your pussy. You cant stop it.” I felt him tense, even felt his cock get bigger as first I felt one warm splash of his cum, deep in pussy, it felt like it was all the way to my womb! Then I felt another splash and another, until he was fully drained.
“ That was good bitch. Lay on the bed, don’t move until I’m ready for another round.” He got off me and walked off to the bathroom and started the shower. I laid there, flipped over onto my back and laid on the bed. Thinking this was the best sex, I ever had. I couldn’t wait for round two. I could only wonder how he would be in the next round, when he wouldn’t be able to cum as fast. I smiled, loving him even more.

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The Internet Cherry

I remember getting my first AOL Massager when I was 11 years old. I know computers were out way before then but I lived a sheltered life and it was the first time my mom even considered getting us a computer. It wasn’t long before I fell hard for the internet and everything it offered.
It all started when I got bored and found a game site where you could play board games and talk to people right there online. The chatting soon directed me to chat rooms and anyone who would talk to an 11 year old female. The normal boring life conversations soon turned into cyber sex. As I didn’t know anything about sex it all started out as questions. Some guys would get angry with me and soon leave. However, others stayed around and took the time to explain the human body to me and what all the sex parts were called. The guys that took the time to teach me soon wanted to call me and talk to me on the phone and I let them. They told me how to rub my clit and when to put a finger inside myself. I started out with a small finger and the more I played and touched the more fingers I could fit. One guy told me to use the handle of my hair brush during one of our phone chats. It felt so good inside of me!
By the time I was 12 years old I had gotten a web cam and was even taking pictures and videotaping myself. I was still a virgin and wanted more than anything to have sex with almost anyone! I was meeting guys from all over the United States that wanted to have cyber sex or phone sex with me. They wanted me to send pictures and/or video tapes. However, I couldn’t find anyone local who would come see me in person.
One evening I was up late talking to a guy named Scott. I had met him a year ago and he always had a new idea of something to try or something he wanted me to do. This evening he wanted me to go into the kitchen and find a straw. I found an old red bendable straw with ripples, the kind you use to get in kids drinks in those plastic cups. Scott guided me in playing with my clit and just holding the straw against my opening but not to let it go inside yet. I opened my pussy lips to show him my clit and how wet I was. I rubbed and pinched my nipples when he asked me to. I sat there in front of my web cam showing him what I was doing as he told me what to do. I rubbed my clit between two fingers and to side to side. I then took one finger and started rubbing little circles until I got very close to cumming. As I got close he then told me to start sliding the straw in and out. I started to use the straw to fuck myself and it felt so great with the ripples in it. As I started to cum I started to pump the straw harder and faster until I felt a sharp pain and froze. I looked down and must have just stood there staring because then next thing I knew Scott was yelling at me to tell him what was wrong. I couldn’t even speak as I raised my hands to show the webcam the blood dripping down my fingers and straw onto the floor.
I must have had the look of fear on my face because Scott then told me in a firm voice that it was alright and I would be ok. His voice became a lot kinder and gently. He told me to go clean up and he’ll wait for me. I did as I was told and quickly cleaned myself up and then came back to take care of the pile of blood still sitting on my floor. I later found out that I had popped my own cherry with the straw. He told me not to worry and that I’ll be alright.
I didn’t really get to talk to Scott again because soon after I met a new guy named Mark. He was everything I thought I wanted. Very nice, cute, and only lived an hour away from me! He had a webcam too so I got to watch the other person for a change. I found out everything I could about him. He was 22 years old and I fell head-over-heels! I would come home from school just to sit on the internet for hours just waiting for him to get online to talk to me. I was like a love sick puppy that couldn’t help but obsess over this guy I thought I knew everything about.
Over time I continued to talk to him as much as I could. Wait for him for hours to get online. No matter how much I begged him though he wouldn’t come and see me…. He told me he would a few times but then would never show. I use to sit up the whole night just waiting for him till I finally feel asleep with my window open. Years went by and I had finally turned 13! I started to give up on Mark and soon started talking to anyone who would talk to me online. I remember having up to 20 or 25 online boyfriends at one time. However, none of them ever found out about the other ones. I had to start keeping a journal just to keep them all straight so none of them could find out. I would sit and talk to 10 to 12 at a time on average. I would have to come up with excuses why my webcam wouldn’t work since I could only let one guy see it at a time. I’ll have cam sex with one and then the other back to back to please them all. Sometimes I’ll cam with one guy and have cyber sex online with the other 10 at the same time.
Till one day I did get caught. Not only did I just get caught but I got caught by the love of my life!!! For some reason the webcam didn’t turn off when I got off with Mark. I turned it on for another guy not knowing that Mark could still see me. When he asked me about it I told him I did the show for him but he didn’t believe me! I guess I wouldn’t believe myself either.
I spent days begging him to take me back and please forgive me. He finally said he would but I was his and only his. I was never to talk to another guy or even date another guy again. I quickly agreed just happy to have Mark back talking to me.
If you would like to hear more please let me know. Thanks 🙂

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Another womans man

She had always though he was sexy and had always wondered what it would be like to be with him but had never done anything about it.