Slave SisterChapter 5 The Raffle
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Cougar Boss Wins Me In A Office Raffle free porn video
In 1972 I had just got out of the Army and was starting college. Don was an old Army buddy from Vietnam and we were both from Chicago so we became good friends in Vietnam. He got wounded once and I stayed with him all night replacing his bandages and guarding him until he could be Medivac out the next morning. Friends like that are hard to come by, so every few weeks or so we would have a few beers together. His dad owned a big machine tool company and Don said he would help me find a summer job. I met with Don’s dad and offered me a job helping an overworked Supervisor of Human Resources (HR). He said go see Ms. Potts and she will fix you up, you start Monday.
Monday came and I was walking around the business side of the factory. I couldn’t help notice all the good looking thirty and forty something women walking around. Most were wearing wedding rings, but I saw that about a third of them weren’t. I went to HR and this dark haired tall well-dressed woman who I guessed was in her mid-forties with a great body for her age. She got up from her desk and asked “I’m Judy are you Tom” and I said yeh I’m your new helper. That’s when I noticed Ms. Potts had a set of 34D tits, they were huge and filled her whole chest. I thought to myself “not bad for a forty five year old, I’d fuck her”.
Well working at Machine Specials Company turned out to be the best thing that had happened to me in years. You see other than a group of aging executives I was the only young guy in the place. I had to admit I was fairly good looking and with me just getting out of the Army I was in great shape. The women at work gave me admiring glances whenever I walked around the halls. After only a few days there I met Angie a nice blond divorced women and dated her a few times and soon I was fucking her. One night I fucked her three times and put two nice loads in her pussy and one in her mouth.
I didn’t know about how women engage in lunch room gossip, but I soon found out. Angie told them all about me and soon I had so many middle aged divorcees and some married women hitting on me every day. By the second month there I was banging three thirty or forty year old divorcees and one gorgeous brunette whose husband was gay.
Well sitting ten feet apart each day from someone you get to know them well. Ms. Potts was a divorcee with two teenage k**s. She had a great outgoing personality; I really grew to like her. She was always k**ding me about my “lifestyle”. I liked being around her, she dressed well and liked to show a lot of cleavage just to tease me. One day she wore an incredibly low cut dress to work and joked, if you don’t stop looking at my tits I’m going to fire you. I replied when I stop looking at beautiful women, shoot me and she just smiled. Women were always finding an excuse to go to in HR about something. She would joke with me and say things like “keep it up and half this office will be pregnant with your k**s” or “I heard a story about you in the lunchroom, but it’s got to be BS, no guy can cum four times in one night”. I replied “well you’re looking at one”. We developed a great rapport and every Monday I would come to work and she would say “how many this weekend?” I would raise three or four fingers. Meaning I had fucked three or four different women that weekend.
Well one day Ms. Potts told me one of the women’s k**s was really sick and the girls in the office are going to have a fundraiser for her. She said we want to make one of the door prizes a date with you”. I laughed and said “count me in” and I’ll pay for the date so more money goes to Angie. Well, the fundraiser was a huge success and it came time for the prize drawing. I came to the front of the room wearing just a pair of tight jeans a tight black T-Shirt and combat boots to show off my muscles. Then they announced “a date with Tom is the third prize, who is holding Ticket No. 789660? A lot of the women were anxiously looking at their tickets when I heard Ms. Potts shout “this is crazy, I got that ticket”. Everybody laughed, but I was kind of glad, I knew she was lonely and she once joked with me that she hadn’t been laid in years. Maybe I could change that.
Well Friday afternoon came and I asked Ms. Potts where do you want to go on Saturday and what time should I pick you up? She named a movie and I suggested we go to a nice dance bar with music afterwards. The movie was a great comedy. As we were walking out to my car I was somewhat surprised when Ms. Potts took my hand as we walked to the car. We drove to a really nice dance club with a good restaurant. Ms. Potts looked stunning. She wore this beautiful blue dress, black nylons and a pair of four inch heels which made her look even taller than she really was. She was teasing me and had unbuttoned the top three buttons of her blouse showing about six inches of cleavage to me. I was glad to accompany such a beautiful older woman to this club. Then she said Tom “my name is Judy, so let’s cut the Ms. Potts stuff, I’m here to have a good time tonight.
Well after a few drinks her somewhat raunchy sense of humor kicked in. Judy said you know it’s hard not to laugh to myself every time I catch you staring at my tits in the office, you try to act like you’re not doing it, but you are. I said “guilty as charged, I would die to see those tits of yours. Judy replied “play your cards right and tonight you might get your wish. Finally, they began playing a slower song and I asked her to dance. I kind of kept a respectable distance apart from her and then Judy put her head on my shoulder and drew her body closer to mine. I held her close and soon our dancing became more romantic. Now those incredible breasts were pressed against my chest and my arm was around her waist. Judy whispered in my ear “I have liked you since the day you stepped in my office” then she turned her head and kissed me briefly on the lips.
We danced about five more times and the passion between us emerged to the surface. I kissed her neck and we turned out heads to exchange short kisses which so went on longer and longer until we were French kissing each other when we sat down between dances. My cock was as hard as a rock and I knew she could feel it pressing against her as we danced. Soon my hand went up her leg almost to her pussy as she occasionally rubbed my cock. I said to myself” Tom you’re 23 and I she is 22 years older than her, are you crazy”. But part of me knew I would be taking Judy to bed tonight and fucking her. She whispered in my ear “it’s been three years since I have been with a man”.
We drove to my house and sat on the couch and began kissing like two teenagers. Judy was moaning softly as I held her close as our hands roamed freely over each other’s bodies as we French kissed. My hand soon wandered down to her chest. I massaged her huge orbs that I had wanted to feel for the past two months. I ran my hand up her dress to her pussy and soon I had two fingers inside her as she moaned softly. Then I found her now swollen clitoris and used my thumb to gently rub it. Judy’s body responded as she began moving back and forth as my hand brought her to a small orgasm. Judy stood up and said “unzip my dress and let’s find your bedroom”. Judy took off her bra and panties as we walked to the room.
Judy lay naked on her back in my bed. My clothes came off and I took her body and moved it so her pussy was right on the edge of the bed. I dropped down on my knees, spread her legs apart and began kissing her inner thigh. Soon I reached her well-groomed pussy. My tongue explored every inch of her beautiful pussy. I parted her labial lips with my tongue which exposed her excited clitoris. I started to kiss it as my fingers entered her pussy; first just one and then two. He hips began gyrating with the movements of my hand as she had a small pre-orgasm. I continued gently sucking on her pussy near her clitoris and the sensitive area just beneath it. She began to pant and her body tensed as she had her first climax in years. I kept up my machinations until I knew she was ready. Then Judy let out a long sigh and said “Tom fuck me, fuck me now”!
Judy rolled over on her back and spread her legs. I looked down at her older but very beautiful body and it excited me even more. Her large breasts made her look rubenesque like the women you see in the old paintings of orgies in Rome. I mounted her and slowly inserted my cock inside her. I was surprised when Judy began moving her hips upward to meet every one of my thrusts into her. I began fucking her faster but she kept pace with me. Then I groaned as I spilled my seed inside her. When she felt the warm sperm enter her she had another orgasm as I continued to slowly fuck her. Then I withdrew and held her closely as we basked in the glow of our first love making session.
Both of us got up and went back to the living room to have a drink and relax. We both knew that we would make love again it was just a matter of how soon. We held each other close and kissed each other. We finished our drinks and Judy got on her knees and used her hand to guide my cock into her mouth. Judy wasted no time and immediately began vigorously sucking the head of my cock concentrating on just the head. Then she worked her way down my shaft licking it and then sucking my cock harder and harder, taking me just to the edge of pure pleasure.
Then Judy turned her head a certain way and took my whole cock in her mouth and deep throated me. But she just didn’t deep throat you like most women do. She put my cock down her throat and just held it there. The sensation of her warm mouth surrounding my entire cock for so long was incredible. Then Judy finally came up for air, and began rapidly fluttering her tongue back and forth around my penis until she reached the spot where the shaft met the head. She lightly sucked it as she flicked her tongue back and forth all around my cock head as I moaned in pleasure. You could tell Judy had sucked a lot of cock in her day and she soon sensed I was ready to cum. That’s when she deep throated my cock and just held it in her mouth. I couldn’t take it anymore and shot a full load of semen down her throat. Judy was a swallower and load after load of my semen went down her throat. Judy stopped came up and kissed me and said “are you surprised, I’ve been sucking cock for thirty years now and I love it”. Especially a nice young hard cock like yours.
We both sat back on the couch to rest but the more I looked at Judy’s body that I had desired for so long my passion rose again. Soon my cock was getting erect again and Judy began softly stroking my cock with her hand. We got up and headed back to the bedroom. I took her body and positioned her so that she was on all fours on the bed. I stood up and slid my organ right into her pussy. Judy started moving back and forth riding my cock as I thrust it inside her. As I entered her, I accidentally found her “G” spot. I began rubbing my cockhead just against this area of her pussy. Judy began screaming so loud I thought someone would call the police. I kept moving my cockhead over her spot as she moaned with each thrust, her whole body was moving in unison every time my cockhead touched her sensitive area. Set let out loud moans as she came again and again. Then her body just went still as every nerve in her body responded to the pleasure I was giving her and she experienced a full vaginal orgasm”. I knew what was happening as Judy’s whole body spasmed as the pleasure centers in every part of her body were overcome with pleasure. I continued to fuck her until she calmed down and fell back exhausted on the bed.
My hands found their way to her incredibly large tits and Judy said “This is what you wanted since the first time you saw me, you love those big tits of mine don’t you? I replied yes, and tonight is my dream come true. Judy said “go ahead enjoy them”. My hand grasped each of her breasts and I gently used my hands to massage her tits. There were even bigger than I thought once I started feeling her up. I took my thumb and began rubbing it across her nipples and she moaned in delight. Then I sucked on one of her nipples as my thumb stimulated the other one. All the while I just felt her huge orbs as she began to respond to my stimulating her breasts. She said ahead take your time and enjoy them. I know you have wanted them for a long time now. I must have made love to her breasts for ten more minutes until I heard her moan as another orgasm swept over her body.
Judy lay back on the bed and we held each other close. She told me if you didn’t fuck around so much with every woman at work, I might consider going out with you. I said “consider it done honey”. I meant it, the only women I wanted now was my 45 year old lover. Not only did I like her but she was the best fuck I’ve had in my short life.
Monday came and I was walking around the business side of the factory. I couldn’t help notice all the good looking thirty and forty something women walking around. Most were wearing wedding rings, but I saw that about a third of them weren’t. I went to HR and this dark haired tall well-dressed woman who I guessed was in her mid-forties with a great body for her age. She got up from her desk and asked “I’m Judy are you Tom” and I said yeh I’m your new helper. That’s when I noticed Ms. Potts had a set of 34D tits, they were huge and filled her whole chest. I thought to myself “not bad for a forty five year old, I’d fuck her”.
Well working at Machine Specials Company turned out to be the best thing that had happened to me in years. You see other than a group of aging executives I was the only young guy in the place. I had to admit I was fairly good looking and with me just getting out of the Army I was in great shape. The women at work gave me admiring glances whenever I walked around the halls. After only a few days there I met Angie a nice blond divorced women and dated her a few times and soon I was fucking her. One night I fucked her three times and put two nice loads in her pussy and one in her mouth.
I didn’t know about how women engage in lunch room gossip, but I soon found out. Angie told them all about me and soon I had so many middle aged divorcees and some married women hitting on me every day. By the second month there I was banging three thirty or forty year old divorcees and one gorgeous brunette whose husband was gay.
Well sitting ten feet apart each day from someone you get to know them well. Ms. Potts was a divorcee with two teenage k**s. She had a great outgoing personality; I really grew to like her. She was always k**ding me about my “lifestyle”. I liked being around her, she dressed well and liked to show a lot of cleavage just to tease me. One day she wore an incredibly low cut dress to work and joked, if you don’t stop looking at my tits I’m going to fire you. I replied when I stop looking at beautiful women, shoot me and she just smiled. Women were always finding an excuse to go to in HR about something. She would joke with me and say things like “keep it up and half this office will be pregnant with your k**s” or “I heard a story about you in the lunchroom, but it’s got to be BS, no guy can cum four times in one night”. I replied “well you’re looking at one”. We developed a great rapport and every Monday I would come to work and she would say “how many this weekend?” I would raise three or four fingers. Meaning I had fucked three or four different women that weekend.
Well one day Ms. Potts told me one of the women’s k**s was really sick and the girls in the office are going to have a fundraiser for her. She said we want to make one of the door prizes a date with you”. I laughed and said “count me in” and I’ll pay for the date so more money goes to Angie. Well, the fundraiser was a huge success and it came time for the prize drawing. I came to the front of the room wearing just a pair of tight jeans a tight black T-Shirt and combat boots to show off my muscles. Then they announced “a date with Tom is the third prize, who is holding Ticket No. 789660? A lot of the women were anxiously looking at their tickets when I heard Ms. Potts shout “this is crazy, I got that ticket”. Everybody laughed, but I was kind of glad, I knew she was lonely and she once joked with me that she hadn’t been laid in years. Maybe I could change that.
Well Friday afternoon came and I asked Ms. Potts where do you want to go on Saturday and what time should I pick you up? She named a movie and I suggested we go to a nice dance bar with music afterwards. The movie was a great comedy. As we were walking out to my car I was somewhat surprised when Ms. Potts took my hand as we walked to the car. We drove to a really nice dance club with a good restaurant. Ms. Potts looked stunning. She wore this beautiful blue dress, black nylons and a pair of four inch heels which made her look even taller than she really was. She was teasing me and had unbuttoned the top three buttons of her blouse showing about six inches of cleavage to me. I was glad to accompany such a beautiful older woman to this club. Then she said Tom “my name is Judy, so let’s cut the Ms. Potts stuff, I’m here to have a good time tonight.
Well after a few drinks her somewhat raunchy sense of humor kicked in. Judy said you know it’s hard not to laugh to myself every time I catch you staring at my tits in the office, you try to act like you’re not doing it, but you are. I said “guilty as charged, I would die to see those tits of yours. Judy replied “play your cards right and tonight you might get your wish. Finally, they began playing a slower song and I asked her to dance. I kind of kept a respectable distance apart from her and then Judy put her head on my shoulder and drew her body closer to mine. I held her close and soon our dancing became more romantic. Now those incredible breasts were pressed against my chest and my arm was around her waist. Judy whispered in my ear “I have liked you since the day you stepped in my office” then she turned her head and kissed me briefly on the lips.
We danced about five more times and the passion between us emerged to the surface. I kissed her neck and we turned out heads to exchange short kisses which so went on longer and longer until we were French kissing each other when we sat down between dances. My cock was as hard as a rock and I knew she could feel it pressing against her as we danced. Soon my hand went up her leg almost to her pussy as she occasionally rubbed my cock. I said to myself” Tom you’re 23 and I she is 22 years older than her, are you crazy”. But part of me knew I would be taking Judy to bed tonight and fucking her. She whispered in my ear “it’s been three years since I have been with a man”.
We drove to my house and sat on the couch and began kissing like two teenagers. Judy was moaning softly as I held her close as our hands roamed freely over each other’s bodies as we French kissed. My hand soon wandered down to her chest. I massaged her huge orbs that I had wanted to feel for the past two months. I ran my hand up her dress to her pussy and soon I had two fingers inside her as she moaned softly. Then I found her now swollen clitoris and used my thumb to gently rub it. Judy’s body responded as she began moving back and forth as my hand brought her to a small orgasm. Judy stood up and said “unzip my dress and let’s find your bedroom”. Judy took off her bra and panties as we walked to the room.
Judy lay naked on her back in my bed. My clothes came off and I took her body and moved it so her pussy was right on the edge of the bed. I dropped down on my knees, spread her legs apart and began kissing her inner thigh. Soon I reached her well-groomed pussy. My tongue explored every inch of her beautiful pussy. I parted her labial lips with my tongue which exposed her excited clitoris. I started to kiss it as my fingers entered her pussy; first just one and then two. He hips began gyrating with the movements of my hand as she had a small pre-orgasm. I continued gently sucking on her pussy near her clitoris and the sensitive area just beneath it. She began to pant and her body tensed as she had her first climax in years. I kept up my machinations until I knew she was ready. Then Judy let out a long sigh and said “Tom fuck me, fuck me now”!
Judy rolled over on her back and spread her legs. I looked down at her older but very beautiful body and it excited me even more. Her large breasts made her look rubenesque like the women you see in the old paintings of orgies in Rome. I mounted her and slowly inserted my cock inside her. I was surprised when Judy began moving her hips upward to meet every one of my thrusts into her. I began fucking her faster but she kept pace with me. Then I groaned as I spilled my seed inside her. When she felt the warm sperm enter her she had another orgasm as I continued to slowly fuck her. Then I withdrew and held her closely as we basked in the glow of our first love making session.
Both of us got up and went back to the living room to have a drink and relax. We both knew that we would make love again it was just a matter of how soon. We held each other close and kissed each other. We finished our drinks and Judy got on her knees and used her hand to guide my cock into her mouth. Judy wasted no time and immediately began vigorously sucking the head of my cock concentrating on just the head. Then she worked her way down my shaft licking it and then sucking my cock harder and harder, taking me just to the edge of pure pleasure.
Then Judy turned her head a certain way and took my whole cock in her mouth and deep throated me. But she just didn’t deep throat you like most women do. She put my cock down her throat and just held it there. The sensation of her warm mouth surrounding my entire cock for so long was incredible. Then Judy finally came up for air, and began rapidly fluttering her tongue back and forth around my penis until she reached the spot where the shaft met the head. She lightly sucked it as she flicked her tongue back and forth all around my cock head as I moaned in pleasure. You could tell Judy had sucked a lot of cock in her day and she soon sensed I was ready to cum. That’s when she deep throated my cock and just held it in her mouth. I couldn’t take it anymore and shot a full load of semen down her throat. Judy was a swallower and load after load of my semen went down her throat. Judy stopped came up and kissed me and said “are you surprised, I’ve been sucking cock for thirty years now and I love it”. Especially a nice young hard cock like yours.
We both sat back on the couch to rest but the more I looked at Judy’s body that I had desired for so long my passion rose again. Soon my cock was getting erect again and Judy began softly stroking my cock with her hand. We got up and headed back to the bedroom. I took her body and positioned her so that she was on all fours on the bed. I stood up and slid my organ right into her pussy. Judy started moving back and forth riding my cock as I thrust it inside her. As I entered her, I accidentally found her “G” spot. I began rubbing my cockhead just against this area of her pussy. Judy began screaming so loud I thought someone would call the police. I kept moving my cockhead over her spot as she moaned with each thrust, her whole body was moving in unison every time my cockhead touched her sensitive area. Set let out loud moans as she came again and again. Then her body just went still as every nerve in her body responded to the pleasure I was giving her and she experienced a full vaginal orgasm”. I knew what was happening as Judy’s whole body spasmed as the pleasure centers in every part of her body were overcome with pleasure. I continued to fuck her until she calmed down and fell back exhausted on the bed.
My hands found their way to her incredibly large tits and Judy said “This is what you wanted since the first time you saw me, you love those big tits of mine don’t you? I replied yes, and tonight is my dream come true. Judy said “go ahead enjoy them”. My hand grasped each of her breasts and I gently used my hands to massage her tits. There were even bigger than I thought once I started feeling her up. I took my thumb and began rubbing it across her nipples and she moaned in delight. Then I sucked on one of her nipples as my thumb stimulated the other one. All the while I just felt her huge orbs as she began to respond to my stimulating her breasts. She said ahead take your time and enjoy them. I know you have wanted them for a long time now. I must have made love to her breasts for ten more minutes until I heard her moan as another orgasm swept over her body.
Judy lay back on the bed and we held each other close. She told me if you didn’t fuck around so much with every woman at work, I might consider going out with you. I said “consider it done honey”. I meant it, the only women I wanted now was my 45 year old lover. Not only did I like her but she was the best fuck I’ve had in my short life.
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